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Volumn , Issue 20, 2008, Pages 3183-3187

Regioselective, solvent-free synthesis of 3-aminoimidazo[1,2-a]pyrimidines under microwave irradiation promoted by zeolite HY

(3) Thompson, Mark J a Hurst, Jenny M a Chen, Beining a

a UNIVERSITY OF SHEFFIELD (United Kingdom)

Author keywords

Bicyclic compounds; Heterocycles; Multicomponent reactions; Regioselectivity; Zeolites

Indexed keywords

EID: 58149361393 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-0028-1087274 Document Type: Article

Times cited : (21)

References (28)

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20
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- The amount of montmorillonite K-10 added proved important; too little gave low conversion, whereas too much resulted in more side reactions and lower isolated yields.
- The amount of montmorillonite K-10 added proved important; too little gave low conversion, whereas too much resulted in more side reactions and lower isolated yields.

21
- 58149360222
- Zeolite Y, hydrogen form, also known as zeolite HY; purchased from Zeolyst International (product ref. CBV400).
- Zeolite Y, hydrogen form, also known as zeolite HY; purchased from Zeolyst International (product ref. CBV400).

22
- 58149356630
- CCDC-693378 (7a), CCDC-693379 (8a) and CCDC-693380 (10) contain the supplementary ciystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request_cif.
- CCDC-693378 (7a), CCDC-693379 (8a) and CCDC-693380 (10) contain the supplementary ciystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request_cif.

23
- 58149341978
- 2-(Trifluoromethyl)benzyl isocyanide and 2-(thiophen-2-yl)ethyl isocyanide were prepared from the requisite amines using a known procedure. 14 Representative experimental procedures for each of the two methods described (Table 1) are detailed below. 2-(4-Methoxyphenyl)-N-(2,4,4-trimethylpentan-2-yl)-imidazo[1,2-a] pyrimidin-3-amine (3a, Method A: 2-Aminopyrimidine (951 mg, 10 mmol, zeolite HY11 (500 mg) and p-anisaldehyde (1.22 mL, 1.36 g, 10 mmol) were mixed in a 100-mL round-bottomed flask, which was supported in a sand bath and placed inside a household microwave oven (800 W power rating, The mixture was irradiated at full power for 3 x 30 s intervals with a 30 s cooling period between heating, during which the flask was swirled gently to allow good mixing of the reagents. Once preformation of the imine was complete, Walborsky's reagent (1.75 mL, 1.39 g, 10 mmol) was added and irradiation was continued for an add
- 18

24
- 0029795527
- Jacobsen, E. J.; Stelzer, L. S.; Belonga, K. L.; Carter, D. B.; Im, W. B.; Sethy, V. H.; Tang, A. H.; von Voigtlander, P. F.; Petke, J. D. J. Med. Chem. 1996, 39, 3820.
- (1996) J. Med. Chem , vol.39 , pp. 3820
- Jacobsen, E.J.¹ Stelzer, L.S.² Belonga, K.L.³ Carter, D.B.⁴ Im, W.B.⁵ Sethy, V.H.⁶ Tang, A.H.⁷ von Voigtlander, P.F.⁸ Petke, J.D.⁹

25
- 58149341983
- Due to their acid sensitivity, compounds containing the 1,1,3,3-tetramethylbutyl group were best columned on basic (2, 3, 5, 6, 9, 10) or neutral (4) alumina, rather than silica, which was suitable for the other examples (7, 8).
- Due to their acid sensitivity, compounds containing the 1,1,3,3-tetramethylbutyl group were best columned on basic (2, 3, 5, 6, 9, 10) or neutral (4) alumina, rather than silica, which was suitable for the other examples (7, 8).

26
- 58149335686
- 4O: 353.2341; found: 353.2348.
- 4O: 353.2341; found: 353.2348.

27
- 58149338415
- 2-(4-Methoxyphenyl)-N-(2,4,4-trimethylpentan-2- yl)imidazo[1,2-a]pyrimidin-3-amine (3a, 1H NMR (400 MHz, CDCl3, δ, 8.58 (dd, 1 H, J, 1.5,6.5 Hz, 8.48-8.51 (m, 1 H, 7.89 (d, 2 H, J, 8.5 Hz, 6.98 (d, 2 H, J, 8.5 Hz, 6.87 (dd, 1 H, J, 4.5, 6.5 Hz, 3.87 (s, 3 H, 3.40 (s, 1 H, 1.60 (s, 2 H, 1.05 (s, 9 H, 0.98 (s, 6 H, 13C NMR (100 MHz, CDCl3, δ, 159.5, 149.3, 144.8, 140.9, 131.1, 129.9, 126.8, 121.2, 113.8, 107.9, 60.9, 57.0, 55.3, 31.8, 31.7, 29.0. IR (solid, 3235, 2924, 2849, 1615, 1504, 1245, 1204, 1030, 786, 764, 498, 485 cm-1. MS ES, m/z, 353 [M, H, HRMS: m/z [M, H, calcd for C21H29N4O: 353.2341; found: 353.2333
- 4O: 353.2341; found: 353.2333.

28
- 58149357811
- 2-Phenyl-N-[2-(trifluoromethyl)benzyl]imidazo[1, 2-a]pyrimidin-3-amine (7a, 1H NMR (400 MHz, CDCl3, δ, 8.45(dd, 1 H, J, 2.0, 4.0 Hz, 8.12 (dd, 1 H, J, 2.0, 6.5 Hz, 8.01-8.06 (m, 2 H, 7.64-7.69 (m, 1 H, 7.40-7.46 (m, 2 H, 7.31-7.39 (m, 3 H, 7.19-7.24 (m, 1 H, 6.75 (dd, 1 H, J, 4.0,6.5 Hz, 4.34 (d, 2 H, J, 6.5 Hz, 3.71 (t, 1 H, J =6.5 Hz, 13C NMR (100 MHz, CDCl3, δ, 149.4, 144.6, 138.2, 137.0, 133.3, 132.2, 131.1, 129.8, 128.6, 128.3 (q, J, 31.5 Hz, 128.0, 127.9, 127.3, 126.3 (q, J, 5.5 Hz, 124.5 (q, J, 270 Hz, 123.2, 108.2, 49.0. 19F NMR (235 MHz, CDCl3, δ, 58.8 (s, IR (solid, 3248, 1612, 1500, 1309, 1116, 762, 692 cm-1. MS ES, m/z, 369 [M, H, HRMS: m/z [M, H, calcd for C20H16F3N4: 36
- 4: 369.1327; found: 369.1331.

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