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

HRID 1242470Notes

Reaction equation

C(=O)=O.C[O:5][C:6]([C:8]1[C:9]([CH2:25][CH2:26][O:27][CH3:28])=[N:10][C:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[N:12][C:13]=1[CH3:14])=O.CC(C[AlH]CC(C)C)C>O1CCCC1>[CH3:28][O:27][CH2:26][CH2:25][C:9]1[C:8]([CH2:6][OH:5])=[C:13]([CH3:14])[N:12]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[N:10]=1

Participants

Conditions

Temperature: -70 °C

Procedure

To a dry-ice cooled solution of 4.9 g (13.83 mmol) 4-(2-methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid methyl ester in 50 ml tetrahydrofurane was dropped 34.57 ml (41.48 mmol) of DIBALH-solution (1.2 M in Toluene). The reaction mixture was stirred for 15 min at −70° C. and then the dry-ice bath was removed, the reaction temperature was allowed to come to RT and the reaction mixture was stirred for 2 h at RT. To the reaction mixture was then dropped carefully, under ice-cooling, 10 ml of 6N HCl. After 4 min was the whole taken up in ether and washed with water. The ether-phase was concentrated under reduced pressure providing 4.67 g pure 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
additionTo the reaction mixture was then dropped carefully, under ice-
temperaturecooling
waitAfter 4 min was
washwashed with water
concentrationThe ether-phase was concentrated under reduced pressure

Sources & evidence

ORD record: ord-68fbf6cdb59a41d0933d137bc2882fb3
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115611B2

Reaction notes

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