Water → 4,5-Dichloro-6-isopropylpyrimidine

HRID 129476Notes

Reaction equation

[CH:1](NC(C)C)(C)C.[Cl:8][C:9]1[C:14]([Cl:15])=[C:13]([CH2:16][CH3:17])[N:12]=[CH:11][N:10]=1.O>O1CCCC1>[Cl:8][C:9]1[C:14]([Cl:15])=[C:13]([CH:16]([CH3:1])[CH3:17])[N:12]=[CH:11][N:10]=1

Participants

Conditions

Temperature: -78 °C

Procedure

N-butyl lithium (1.6 mol solution in hexane, 19.4 ml) is added dropwise at 0° C., under a nitrogen atmosphere, to a solution of diisopropylamine (4.4 ml) in tetrahydrofuran (100 ml), and the mixture is stirred for 20 minutes. The solution is cooled to -78° C. and then 5 g of 4,5-dichloro-6-ethylpyrimidine in solution in 10 ml of tetrahydrofuran are added dropwise. The mixture is stirred at -78° C. for one hour and then brought to room temperature over a period of 2 hours. After the addition of water (200 ml), the mixture is extracted with ethyl acetate and the organic phase is dried over sodium sulfate and concentrated. Chromatography on silica gel (eluant: ethyl acetate/hexane 1:10) yields 3.8 g (71% of the theoretical yield) of 4,5-dichloro-6-isopropylpyrimidine in the form of a yellow oil.

Workup

stirringThe mixture is stirred at -78° C. for one hour
waitbrought to room temperature over a period of 2 hours
extractionthe mixture is extracted with ethyl acetate
dry with materialthe organic phase is dried over sodium sulfate
concentrationconcentrated
customChromatography on silica gel (eluant: ethyl acetate/hexane 1:10) yields 3.8 g (71% of the

Sources & evidence

ORD record: ord-446fd09f7f8242c8a4184ea50130ff89
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05468751

Reaction notes

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