4,6-Dichloro-5-methylpyrimidine → 4-Chloro-5-methyl-6-(1-(pyrimidin-2-yl)piperidin-4-yloxy)pyrimidine

HRID 1619443Notes

Reaction equation

CC(C)([O-])C.[K+].[N:7]1[CH:12]=[CH:11][CH:10]=[N:9][C:8]=1[N:13]1[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]1.[Cl:20][C:21]1[C:26]([CH3:27])=[C:25](Cl)[N:24]=[CH:23][N:22]=1>C1COCC1>[Cl:20][C:21]1[C:26]([CH3:27])=[C:25]([O:19][CH:16]2[CH2:15][CH2:14][N:13]([C:8]3[N:9]=[CH:10][CH:11]=[CH:12][N:7]=3)[CH2:18][CH2:17]2)[N:24]=[CH:23][N:22]=1

Participants

Conditions

Temperature: 30 °C

Procedure

Potassium tert-butoxide (2.86 gm, 0.01397 moles) was added to an ice-cold solution of 1-(pyrimidin-2-yl)piperidin-4-ol (2.50 gm, 0.01397 moles) and 4,6-dichloro-5-methylpyrimidine (2.27 mg, 0.01397 moles) in dry THF (15 ml) and the reaction mixture was stirred for 5 hours at 30° C. The reaction mixture was poured into ice cold water, solid precipitated was filtered and dried under vacuum to obtain 140 mg of product.

Workup

additionThe reaction mixture was poured into ice cold water, solid
customprecipitated
filtrationwas filtered
customdried under vacuum

Sources & evidence

ORD record: ord-52999f5c34234070939fbe00122f346c
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772302B2

Reaction notes

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