Methyl iodide → HCID 57747383, compound

HRID 222086Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][C:10]2[C:11]3[NH:34][CH:33]=[CH:32][C:12]=3[N:13]=[C:14]([N:16]([C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[N:15]=2)=[C:4]([CH3:35])[CH:3]=1.[Li+].[CH3:37][Si]([N-][Si](C)(C)C)(C)C.IC>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH3:35])[C:5]([S:9][C:10]2[C:11]3[N:34]([CH3:37])[CH:33]=[CH:32][C:12]=3[N:13]=[C:14]([N:16]([C:24]3[CH:25]=[CH:26][C:27]([C:30]#[N:31])=[CH:28][CH:29]=3)[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[N:15]=2)=[C:6]([CH3:8])[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold mixture of tert-butyl 4-(4-bromo-2,6-dimethylphenylthio)-5H-pyrrolo[3,2-d]pyrimidin-2-yl(4-cyanophenyl)carbamate (1.5 mmol) in THF (5 ml) at −78° C. is added a solution of LiHMDS (2 mmol). The mixture is warmed to 0° C. over 2 hours and then cooled to −78° C. Iodomethane (6 mmol) is added and the mixture warmed to room temperature over 2 hours and then stirred at room temperature for an additional 2 hours. The mixture is washed with brine and extracted with ethyl acetate (×3). The combined organic layers are dried over MgSO4 and concentrated to dryness. The crude material is purified by chromatography on silica.

Workup

temperaturecooled to −78° C
temperaturethe mixture warmed to room temperature over 2 hours
washThe mixture is washed with brine
extractionextracted with ethyl acetate (×3)
dry with materialThe combined organic layers are dried over MgSO4
concentrationconcentrated to dryness
customThe crude material is purified by chromatography on silica

Sources & evidence

ORD record: ord-d6e4a2a4bac0472e9207bdc0c50eaf14
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207178B2

Reaction notes

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