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Synlett
Volumn , Issue 18, 2008, Pages 2799-2802
An efficient one-pot synthetic method for 2,4-disubstituted 7-arylpyrido [4,3-d]pyrimidines from 2,4-disubstituted 6-(arylethynyl)pyrimidine-5- carbaldehydes and tert-butylamine
Author keywords

1,6 electrocyclic reaction; Aldehydes; Alkynes; Cyclization; Pyrido 4,3 d pyrimidines
Indexed keywords

ALDEHYDE DERIVATIVE; BUTYLAMINE; PYRIMIDINE DERIVATIVE;
EID: 56849106799     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1083500     Document Type: Article
Times cited : (5)
References (24)
  • 1
    • 0003799267 scopus 로고
    • Stang, P. J, Diederich, F, Eds, VCH: Weinheim
    • (a) Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Eds.; VCH: Weinheim, 1995.
    • (1995) Modern Acetylene Chemistry
  • 20
    • 56849124485 scopus 로고    scopus 로고
    • Typical Procedure for the Preparation of 2,4-Disubstituted 7-Arylpyrido[4,3-d]pyrimidines 2a-u The mixture of the corresponding 2,4-disubstituted 6-(arylethynyl)pyrimidine-5-carbaldehyde 1a-u (0.2 mmol) and t-BuNH2 (3 mL) in tube was flushed with argon, and the tube was carefully sealed. The mixture was heated at 110-120°C for 24 h. The solvent was evaporated under reduced pressure, residue recrystallized to give compounds 2a-u. 2-(Methylthio)-4-morpholin-1- yl-7-phenylpyrido[4,3-d]pyrimidine (2b) Yield 95, mp 145-147°C (from 2-PrOH, 1H NMR (300 MHz, CDCl3, δ, 2.66 (3 H, s, SCH3, 3.93 [4 H, t, J, 3.9 Hz, N(CH2)2, 4.01 [4 H, t, J, 3.9 Hz, O(CH 2)2, 7.49-7.55 (3 H, m, ArH, 7.95 (1 H, s, CH, 8.13-8.16 (2 H, m, ArH, 9.27 (1 H, s, CH, 13C NMR 75 Hz, CDCl 3, δ, 14.3, 49.8, 66
    • 4OS: C, 65.55; H, 6.05; N, 15.29. Found: C, 65.76; H, 5.93; N, 15.44.
  • 21
    • 56849093554 scopus 로고    scopus 로고
    • Typical Procedure for the Preparation of N-{4, Z)-2-(tert-butylamino, 2-phenylvinyl]-2-(methylthio)pyrimidin-5-ylmethylene}-2-methylpropan-2-amines 3a-c The mixture of the corresponding 2,4-disubstituted 6-(arylethynyl) pyrimidine-5-carbaldehyde 1a-c (0.2 mmol) and t-BuNH2 (3 mL) in tube was flushed with argon, and the tube was carefully sealed. The mixture was heated at 80-90°C for 20 h. The solvent was evaporated under reduced pressure, compounds 3a-c were isolated by column flash chromatography. N-{4-(Z)-2, tert-burylamino)-2-phenylvinyl]-2-(methylthio)-6-morpholin-1-ylpyrimidin-5- ylmethylene}-2-methylpropan-2-amine (3b) Yield 62, mp 140-142°C (from MeOH-H2O, Rf, 0.78 (toluene-EtOAc, 1:1, IR (KBr, 3442 (NH) cm-1. 1H NMR (300 MHz, CDCl3, δ, 1.19 9 H, s, t-Bu
    • 5OS: C, 66.77; H, 7.97; N, 14.95. Found: C, 66.49; H, 8.08; N, 15.10.
  • 22
    • 56849126962 scopus 로고    scopus 로고
    • N-{4-(Z)-2, tert-burylamino, 2-phenylvinyl]-2-(methylthio)-6-piperidin-1-ylpyrimidin-5-ylmethylene, 2-methylpropan-2-amine (3c) Yield 58, mp 109-110°C (from 2-PrOH, Rf, 0.81 (toluene-EtOAc, 1:1, IR (KBr, 3443 (NH) cm -1. 1H NMR (300 MHz, CDCl3, δ, 1.17 (9 H, s, t-Bu, 1.23 (9 H, s, t-Bu, 1.65 [6 H, br s, CH 2)3, 2.57 (3 H, s, SCH3, 3.41 [4 H, br s, N(CH2)2, 6.31 (1 H, s, CH, 7.32-7.34 (3 H, m, ArH, 7.48-7.51 (2 H, m, ArH, 8.07 (1 H, s, CH, 9.98 (1 H, br s, NH, 1H NMR (300 MHz, DMSO-d6, δ, 1.09 (9 H, s, t-Bu, 1.14 (9 H, s, t-Bu, 1.61 [6 H, br s, CH2)3, 2.52 (3 H, s, SCH3, 3.37 [4 H, br s, N(CH2)2, 6.50 (1 H, s, CH, 7.40 (5 H, s, ArH, 7.99 (1 H, s, CH, 9.88 1 H, br s, NH
    • 5S: C, 69.63; H, 8.44; N, 15.04. Found: C, 69.42; H, 8.59; N, 15.19.
  • 23
    • 56849101843 scopus 로고    scopus 로고
    • 2O (10 mL), precipitate collected by filtration and recrystallyzed to give compounds 2a-c.
    • 2O (10 mL), precipitate collected by filtration and recrystallyzed to give compounds 2a-c.
  • 24
    • 56849087455 scopus 로고    scopus 로고
    • 13C NMR spectroscopic and microanalytical data.
    • 13C NMR spectroscopic and microanalytical data.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.