Carbon tetrabromide → 4-(2-Bromo-1,3-thiazol-5-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 40903Notes

Reaction equation

C([Li])CCC.[S:6]1[C:10]([C:11]2[C:12]3[CH:19]=[CH:18][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:13]=3[N:14]=[CH:15][N:16]=2)=[CH:9][N:8]=[CH:7]1.C(Br)(Br)(Br)[Br:29]>CCCCCC.C1COCC1>[Br:29][C:7]1[S:6][C:10]([C:11]2[C:12]3[CH:19]=[CH:18][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:13]=3[N:14]=[CH:15][N:16]=2)=[CH:9][N:8]=1

Participants

Conditions

Temperature: -78 °C

Procedure

2.5 M n-Butyllithium in hexane (0.860 mL) was added dropwise to a −78° C. solution of 4-(1,3-thiazol-5-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine (550 mg, 0.0016 mol) in THF (20 mL). The mixture was stirred for 30 minutes at −78° C., followed by the slow addition of carbon tetrabromide (658 mg, 0.00198 mol) as a solution in THF (10 mL). After 30 minutes, the mixture was quenched with a small amount of saturated ammonium chloride, diluted with ether, and dried over sodium sulfate. The residue obtained after filtration and concentration was purified by flash column chromatography (ethyl acetate/hexanes) to afford the desired product (387 mg, 57%).

Workup

waitAfter 30 minutes
customthe mixture was quenched with a small amount of saturated ammonium chloride
additiondiluted with ether
dry with materialdried over sodium sulfate
customThe residue obtained
filtrationafter filtration and concentration
customwas purified by flash column chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-f6378f1eec7847bba2dca4a2663d5c57
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530485B2

Reaction notes

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