Carbon Dioxide → [4-(2-Methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol

HRID 890469Notes

Reaction equation

CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.C(=O)=O.C[O:21][C:22]([C:24]1[C:25]([CH2:41][CH2:42][O:43][CH3:44])=[N:26][C:27]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=2)=[N:28][C:29]=1[CH3:30])=O>O1CCCC1>[CH3:44][O:43][CH2:42][CH2:41][C:25]1[C:24]([CH2:22][OH:21])=[C:29]([CH3:30])[N:28]=[C:27]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=2)[N:26]=1

Participants

Conditions

Temperature: -70 °C

Procedure

A 1.2 M solution of DIBALH in toluene (34.6 ml, 41.5 mmol) was added dropwise to a dry-ice cooled solution of 4-(2-methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid methyl ester (4.9 g, 13.8 mmol) in tetrahydrofuran (50 ml). The reaction mixture was stirred for 15 min at −70° C., the dry-ice bath was removed and the reaction temperature was allowed to come to RT. The reaction mixture was stirred for 2 h at RT. Under ice-cooling 6 N aqueous HCl (10 ml) was carefully added. After 4 min ether was added, the layers were separated and the organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure to give 4.67 g (14.3 mmol, quant.) of crystalline [4-(2-methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol.

Workup

customthe dry-ice bath was removed
customto come to RT
stirringThe reaction mixture was stirred for 2 h at RT
temperatureUnder ice-cooling 6 N aqueous HCl (10 ml)
additionwas carefully added
additionAfter 4 min ether was added
customthe layers were separated
washthe organic layer was washed with water
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-f1be82090dc9466ea2abacdd59029b69
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06995263B2

Reaction notes

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