Diisopropylamine → 1-(3-Bromophenyl)-2-(2-methylthiopyrimidin-4-yl)-ethanone

HRID 496656Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][S:14][C:15]1[N:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]=1.[Br:22][C:23]1[CH:24]=[C:25]([CH:32]=[CH:33][CH:34]=1)[C:26](N(OC)C)=[O:27]>O1CCCC1.C(OCC)(=O)C.O>[Br:22][C:23]1[CH:24]=[C:25]([C:26](=[O:27])[CH2:21][C:19]2[CH:18]=[CH:17][N:16]=[C:15]([S:14][CH3:13])[N:20]=2)[CH:32]=[CH:33][CH:34]=1

Participants

Conditions

Temperature: -75 °C

Procedure

19.8 ml (140 mmol) diisopropylamine were dissolved in 250 ml dry tetrahydrofurane and cooled to −75° C. and 87.6 ml of a solution of n-butyllithium (1.6 M in hexane, 140 mmol) was added over a period of 20 minutes. After stirring for 15 minutes at −75° C. a solution of 13.1 g (93 mmol) 2-methylthio-4-methylpyrimidine in 80 ml dry tetrahydrofurane was added within 30 minutes at −75° C. and the mixture was stirred for additional 15 minutes. Then a solution of 25.1 g (103 mmol) B1 was added within 30 minutes at −75° C. The mixture was allowed to warm up to room temperature and was poured on 600 ml ethyl acetate/water (1:1). The aqueous layer was extracted with 50 ml ethyl acetate and the combined organic layers were dried over sodium sulphate. Removal of the solvent in vacuo yielded 23.3 g (77%) C1, m.p. 98-101° C.

Workup

additionwas added within 30 minutes at −75° C.
temperatureto warm up to room temperature
extractionThe aqueous layer was extracted with 50 ml ethyl acetate
dry with materialthe combined organic layers were dried over sodium sulphate
customRemoval of the solvent in vacuo

Sources & evidence

ORD record: ord-6536fe6e8876411f89289e3ebde085c3
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06946471B2

Reaction notes

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