4-Chloro-2,6-dimethoxypyrimidine → HCID 24748349, compound

HRID 605659Notes

Reaction equation

HRID 605659 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:32]=[C:31]([O:33][CH3:34])[N:30]=[C:29]([O:35][CH3:36])[N:28]=2)=[CH:25][N:26]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(C(C)(C)C)(C)C.[Si](OC(C1OC([Sn](CCCC)(CCCC)CCCC)=CN=1)CCCCCCC1C=CC=CC=1)(C(C)(C)C)(C)C.ClC1N=C(OC)N=C(OC)C=1>>[CH3:36][O:35][C:29]1[N:28]=[C:27]([C:24]2[O:23][C:22]([C:9](=[O:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:26][CH:25]=2)[CH:32]=[C:31]([O:33][CH3:34])[N:30]=1

Participants

4

Reactant 3

HCID 806004-Chloro-2,6-dimethoxypyrimidineHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazoleHCID 67046069HCID 67046069, compound

Product 1

HCID 24748349HCID 24748349, compoundYield 90%

Procedure

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(2,6-dimethoxypyrimidin-4-yl)oxazole. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (200 mg, 0.302 mmol) and 6-chloro-2,4-dimethoxypyrimidine following General Procedure A. Flash chromatography (10% EtOAc/hexanes) yielded the title compound as a thick oil (138 mg, 90%): 1H NMR (CDCl3, 400 MHz) 6 7.73 (s, 1H), 7.28-7.24 (m, 2H), 7.18-7.15 (m, 3H), 6.67 (s, 1H), 4.85 (dd, 1H, J=7.3, 5.9 Hz), 4.03 (s, 3H), 4.00 (s, 3H), 2.59 (t, 2H, J=7.6 Hz), 1.96 (m, 2H), 1.62 (m, 2H), 1.36 (m, 4H), 0.90 (s, 9H), 0.10 (s, 3H), 0.00 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 172.3, 166.6, 165.4, 155.2, 149.0, 142.6, 128.3, 128.1, 128.0, 125.5, 95.8, 68.6, 54.8, 53.9, 36.2, 35.8, 31.3, 29.0, 25.6, 25.6, 24.9, 18.1, −5.1, −5.2.

Sources & evidence

ORD record
ord-8fcf90281f1849fc99873c0d9beb6106
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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