5-Iodo-2,4-dimethoxypyrimidine → HCID 24748380, compound

HRID 605661Notes

Reaction equation

HRID 605661 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[C:28]([O:35][CH3:36])=[N:29][C:30]([O:33][CH3:34])=[N:31][CH:32]=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.IC1C=NC(OC)=NC=1OC>>[CH3:34][O:33][C:30]1[N:29]=[C:28]([O:35][CH3:36])[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][N:31]=1

Participants

4

Reactant 3

HCID 2634165-Iodo-2,4-dimethoxypyrimidineHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazoleHCID 67046888HCID 67046888, compound

Product 1

HCID 24748380HCID 24748380, compoundYield 83%

Procedure

2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(2,4-dimethoxypyrimidin-5-yl)oxazole. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (130 mg, 0.196 mmol) and 5-iodo-2,6-dimethoxypyrimidine following General Procedure A. Flash chromatography (10% EtOAc/hexanes) yielded the title compound as a thick oil (85 mg, 83%): 1H NMR (CDCl3, 400 MHz) δ 8.67 (s, 1H), 7.34 (s, 1H), 7.28-7.24 (m, 2H), 7.18-7.14 (m, 3H), 4.85 (dd, 1H, J=7.4, 5.9 Hz), 4.13 (s, 3H), 4.05 (s, 3H), 2.59 (t, 2H, J=7.8 Hz), 1.93 (m, 2H), 1.60 (m, 2H), 1.41 (m, 4H), 0.89 (s, 9H), 0.09 (s, 3H), 0.01 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 166.4, 164.3, 154.1, 143.9, 142.7, 128.3, 128.1, 125.5, 125.2, 104.9, 68.5, 55.0, 54.4, 36.3, 35.8, 31.3, 29.1, 25.6, 25.6, 25.0, 18.1, −5.0, −5.2.

Sources & evidence

ORD record
ord-e8037edf6cc64384853309cf4a449ad0
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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