SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 10, 2008, Pages 1510-1514

Synthesis of 8-heteroaryl-2′-deoxyguanosine derivatives

(4) Hobley, Gerard a Gubala, Vladimir a Rivera Sánchez, María Del C a Rivera, José M a

a UNIVERSITY OF PUERTO RICO (Puerto Rico)

Author keywords

Coupling; Nucleobases; Nucleosides; Palladium; Stille reaction

Indexed keywords

8 BROMO 2' DEOXYGUANOSINE; ALKYL GROUP; BORONIC ACID DERIVATIVE; DEOXYGUANOSINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDINE DERIVATIVE; TIN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; MICROWAVE IRRADIATION; QUANTUM YIELD; REACTION ANALYSIS; STILLE REACTION; SUZUKI MIYAURA REACTION; SYNTHESIS;

EID: 46449111714 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-1077795 Document Type: Article

Times cited : (16)

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42
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- 1H NMR
- 1H NMR

43
- 46449136272
- 6): δ = 10.89
- 6): δ = 10.89

44
- 46449127671
- br s, 1 H, 8.85 (d, J, 2 Hz, 1 H, 8.71 (dd, J, 5, 1 Hz, 1 H, 8.09 (dt, J, 8, 2 Hz, 1 H, 7.59 (dd, J, 8, 5 Hz, 1 H, 6.50 (s, 2 H, 6.06 (t, J, 7 Hz, 1 H, 5.19 (d, J, 5 Hz, 1 H, 4.96 (t, J, 6 Hz, 1 H, 4.33 (br m, 1 H, 3.80 (m, 1 H, 3.64 (m, 1 H, 3.53 (m, 1 H, 3.17 (m, 1 H, 2.08 (ddd, J, 13, 6, 2 Hz, 1 H, 13C NMR (80MHz,DMSO-d6, δ, 174.1, 173.6, 153.7, 151.1, 149.6, 118.8, 115.9, 83.3, 79.8, 72.1, 61.1, 31.9, 31.2, 27.1, 16.5. IR (neat, 3206, 1677, 1631, 1560, 1244 cm-1. Anal. Calcd for C15H16N6O4: C, 52.32; H, 4.68; N, 24.41. Found: C, 51.65; H, 4.73; N, 24.16. Compound 2b: white solid, yield 88, 164 mg, 304 μmol, mp 203 °C. 1H NMR (500 MHz, DMSO-d6, δ, 10.87 (s, 1 H, 8.05 (m, 1 H, 7.97 (m, 1 H, 7.94 (s, 1 H, 7.46 (m, 2 H, 6.59 (s, 2 H, 6.45 t, J, 7 Hz
- 13C NMR

45
- 46449116053
- -1.
- -1.

46
- 11144325118
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47
- 46449130232
- 2O-MeCN-DMF (2:1:1). The corresponding boronic acid
- 2O-MeCN-DMF (2:1:1). The corresponding boronic acid

48
- 46449123330
- 0.5 equiv of Id) was added and the mixture irradiated with microwaves at 100 W, 120 °C with constant cooling for 5 min. The addition of the boronic acid and microwave irradiation was repeated until TLC revealed that the starting material was consumed. The reaction mixture was then poured into H2O (25 mL) and pH was adjusted to 6-7 (0.1 M HC1, The precipitate formed was stirred at 0 °C for another 30 min, filtered, and dried in vacuo to give compound 2d as a solid. Analytical Data Compound 2d: yield 77, 88.2 mg, 265 umol, 1H NMR (500 MHz, DMSO-d6, δ, 10.81 (s, 1 H, 7.75 (d, J, 6 Hz, 1 H, 7.50 (d, J, 4 Hz, 1 H, 7.22 (dd, J, 5, 4 Hz, 1 H, 6.47 (s, 2 H, 6.27 (t, J, 8 Hz, 1 H, 5.20 (d, J, 5 Hz, 1 H, 4.96 (t, J, 5 Hz, 1 H, 4.39 (d, J, 3 Hz, 1 H, 3.83 (t, J, 3 Hz, 1 H, 3.64 (m, 1 H, 3.54 (m, 1 H, 3.33 (m, 1 H, 2.09 m, 1 H
- -1.

49
- 46449127967
- Esterifications were performed according to the procedures outlined in ref. 8. Analytical Data Compound 3a: yield 89, 63.0 mg, 129 μmol, mp 126 °C. 1H NMR (500 MHz, DMSO-d6, δ, 11.0 (br s, 1 H, 8.88 (d, J, 2 Hz, 1 H, 8.74 (dd, J, 5, 1 Hz, 1 H, 8.10 (d, J, 8 Hz, 1 H, 7.68 (dd, J, 5, 8 Hz, 1 H, 6.61 (s, 2 H, 6.13 (t, J, 7 Hz, 1 H, 5.50 (q, J, 3 Hz, 1 H, 4.45 (dd, J, 11, 5 Hz, 1 H, 4.30 (dd, J, 11, 7 Hz, 1 H, 4.20 (m, 1 H, 3.57 (q, J, 7 Hz, 1 H, 2.57 (m, 2 H, 2.44 (q, J, 5 Hz, 1 H, 1.12 (d, J, 2 Hz, 1 H)1.10 (s, 6 H, 1.08 (s, 3 H, 13C NMR (125 MHz, DMSO-d6, δ, 176.0, 175.7, 156.7, 153.3, 152.1, 150.2, 139.3, 144.2, 136.5, 126.3, 123.6, 117.4, 84.72, 81.8, 74.7, 63.5, 34.0, 33.1, 33.0, 18.71, 18.68, 18.60, 18.59. IR neat, 1727, 1689, 1627, 1150 cm-1. Anal. Calcd for C23
- 6): δ = 10.88

50
- 46449092689
- s, 1 H, 7.90 (d, J, 5 Hz, 1 H, 6.96 (d, J, 5 Hz, 1 H, 6.69 (dd, J, 5, 4 Hz, 1 H, 6.54 (s, 2 H, 6.44 (t, J, 7 Hz, 1 H, 5.46 (m, 1 H, 4.40 (m, 1 H, 4.22 (m, 1 H, 4.16 (m, 1 H, 3.50 (m, 1 H, 2.57 (m, 2 H, 2.41 (m, 1 H, 1.12 (m, 6 H, 1.03 (m, 6 H, 13C NMR (125 MHz, DMSO-d6):δ= 176.6, 176.3, 157.1, 153.9, 152.3, 145.1, 144.7, 138.4, 117.9, 112.9, 112.5, 85.1, 82.3, 75.3, 64.3, 35.0, 33.7, 19.3. IR (neat1, 1732, 1681, 1153, 1077, 764 cm-1. Anal. Calcd for C22H27N5O7: C, 55.81; H, 5.75; N, 14.79. Found: C, 55.44; H, 6.02; N, 14.67. Compound 3f: yellow solid, yield 80, 228 mg, 481 μmol, 1H NMR (500 MHz, DMSO-d6, δ, 10.83 (br s, 1 H, 8.14 (s, 1 H, 7.87 (t, J, 1 Hz, 1 H, 6.88 (d, J, 1 Hz, 1 H, 6.50 (br s, 2 H, 6.22 (t, 1 H, 5.49 (quin, J, 7, 4 Hz, 1 H, 4.40 m, 1 H, 4
- -1.

51
- 46449101974
- General Procedure for a Stille Coupling Using the Synthesis of Compound 4a as an Example 3′,5′-i-Bu-8-BrdG (50.0 mg, 103 μmol, DPPP (6.35 mg, 15.4 μmol, Pd(OAc)2 (3.45 mg, 15.4 μmol, Cu2O (29.5 mg, 206 μmol, and NMP (490 μL) were mixed. After this, compound 6a (115 mg, 206 μmol) was added to the mixture. The mixture was heated to 115 °C for 1 h after which HPLC analysis of the crude reaction mixture showed that the starting material was consumed. Therefore, the mixture was filtered through Celite and the solvents removed under reduced pressure. The product was isolated by column chromatography (50% EtOAc in Et2O) yielding 4a as a white solid. Analytical Data Compound 4a: white solid, yield 74, 47.0 mg, 75.9 μmol, mp 169 °C. 1H NMR (500 MHz, DMSO-d6, δ, 10.89 (s, 1 H, 8.02 (m, 2 H, 7.58 (m, 2 H, 7.36 (m, 4 H, 7.30 (m, 1 H, 6.54 s
- 7Si: C, 56.66; H, 6.89; N, 13.67. Found: C, 56.59; H, 6.89; N, 12.85.

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