Ammonium Chloride → HCID 86759690, compound

HRID 2179941Notes

Reaction equation

C([Sn](CCCC)(CCCC)[C:6]1[N:11]=[CH:10][CH:9]=[CH:8][N:7]=1)CCC.C([Li])CCC.[CH3:25][N:26]([CH2:34][CH2:35][CH:36]=[O:37])[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30].[Cl-].[NH4+]>O1CCCC1>[OH:37][CH:36]([C:6]1[N:7]=[CH:8][CH:9]=[CH:10][N:11]=1)[CH2:35][CH2:34][N:26]([CH3:25])[C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:32])[CH3:31]

Participants

Conditions

Temperature: -78 °C

Procedure

To 2-(tributylstannyl)pyrimidine (690 mg, 1.87 mmol) dissolved in dry tetrahydrofuran (10 ml) cooled to −78° C. was added 2.4M n-butyl lithium in hexanes (0.8 ml, 1.87 mmol) under nitrogen. After stirring for a further 0.5 h, methyl(3-oxopropyl)carbamic acid, 1,1-dimethylethyl ester in dry tetrahydrofuran (10 ml) was added rapidly at −78° C. The reaction mixture was allowed to warm to ambient, treated with aqueous saturated ammonium chloride solution and extracted with ethyl acetate which was washed with brine and dried over anhydrous magnesium sulphate. The solvent was evaporated and the residue eluted down a flash chromatography column using initially 10% ethyl acetate/dichloromethane, then 10% methanol/dichloromethane to give 260 mg (43%) of the subtitle compound as a viscous yellow oil.

Workup

temperatureto warm to ambient,
extractionextracted with ethyl acetate which
washwas washed with brine
dry with materialdried over anhydrous magnesium sulphate
customThe solvent was evaporated
washthe residue eluted down a flash chromatography column

Sources & evidence

ORD record: ord-8ac22a428f5e431b8b517ce2cef8fb31
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06887871B2

Reaction notes

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