Diisobutylaluminum hydride → [4-Cyclopropyl-6-methoxymethyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol

HRID 1242457Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:6]([CH:24]2[CH2:26][CH2:25]2)=[N:7][C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)=[N:9][C:10]=1[CH2:11][O:12][CH3:13])=O.CC(C[AlH]CC(C)C)C>O1CCCC1>[CH:24]1([C:6]2[C:5]([CH2:3][OH:2])=[C:10]([CH2:11][O:12][CH3:13])[N:9]=[C:8]([C:14]3[CH:15]=[CH:16][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:18][CH:19]=3)[N:7]=2)[CH2:26][CH2:25]1

Participants

Conditions

Temperature: -70 °C

Procedure

To a solution of 2.86 g (7.8 mmol) 4-cyclopropyl-6-methoxymethyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid methyl ester in 30 ml tetrahydrofurane was dropped at −78° C., 20 ml (24 mmol) of a DIBALH-solution (1.2 M in toluene). The reaction was stirred for 15 min at −70° C., then the dry-ice bath was removed, the reaction temperature was allowed to come to RT and the solution was stirred for 2 h at RT. To the reaction mixture was then dropped carefully, under ice-cooling, 13 ml of 6N HCl. The reaction mixture was then taken up in ether and was washed with water. The ether-phase was concentrated under reduced pressure providing 1.29 g of pure crystalline [4-cyclopropyl-6-methoxymethyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol.

Workup

customthe dry-ice bath was removed
customto come to RT
stirringthe solution was stirred for 2 h at RT
additionTo the reaction mixture was then dropped carefully, under ice-
temperaturecooling
washwas washed with water
concentrationThe ether-phase was concentrated under reduced pressure

Sources & evidence

ORD record: ord-a83434081efb4353a9411c2e4342bdfe
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115611B2

Reaction notes

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