Sodium Bicarbonate → (4-Benzyloxy-3,5-dimethyl-phenyl)-(6-chloro-pyrimidin-4-yl)-methanone

HRID 469302Notes

Reaction equation

C([Li])CCC.[CH2:6]([O:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17](Br)=[CH:16][C:15]=1[CH3:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CON(C)[C:26]([C:28]1[CH:33]=[C:32]([Cl:34])[N:31]=[CH:30][N:29]=1)=[O:27].C(=O)([O-])O.[Na+]>C1COCC1>[CH2:6]([O:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([C:26]([C:28]2[CH:33]=[C:32]([Cl:34])[N:31]=[CH:30][N:29]=2)=[O:27])=[CH:16][C:15]=1[CH3:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: -75 °C

Procedure

Under an argon atmosphere 2.8 mL (4.5 mmol) of a 1.6 M n-butyllithium solution were added to a mixture of 1.2 g (4.0 mmol) 2-benzyloxy-5-bromo-1,3-dimethyl-benzene in mL THF cooled to −75° C. and the mixture was stirred for 1 h at −75° C. Then 0.96 g (4.3 mmol) 6-chloro-pyrimidine-4-carboxylic acidmethoxy-methyl-amide, dissolved in 10 mL THF, were added dropwise. After another 30 min stirring at −75° C. the reaction mixture was slowly heated to 0° C. The mixture was combined with saturated sodium hydrogen carbonate solution and extracted with diethyl ether. The organic phase was dried and evaporated down. The residue was purified by flash chromatography.

Workup

additionwere added dropwise
stirringAfter another 30 min stirring at −75° C. the reaction mixture
temperaturewas slowly heated to 0° C
extractionextracted with diethyl ether
customThe organic phase was dried
customevaporated down
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-511a463b0c884810943719051e0c5e50
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629137B2

Reaction notes

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