Carbon Dioxide → [4-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol

HRID 890427Notes

Reaction equation

CC(C[AlH]CC(C)C)C.C(=O)=O.C([O:15][C:16]([C:18]1[C:19]([CH:34]2[CH2:36][CH2:35]2)=[N:20][C:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)=[N:22][CH:23]=1)=O)C>C1(C)C=CC=CC=1.C1COCC1.CCOCC>[CH:34]1([C:19]2[C:18]([CH2:16][OH:15])=[CH:23][N:22]=[C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:26][CH:25]=3)[N:20]=2)[CH2:36][CH2:35]1

Participants

Conditions

Temperature: -50 °C

Procedure

Within 10 min 31.6 ml (37.9 mmol) of a 1.2 M DIBALH solution in toluene were added dropwise to a dry ice cooled (−50° C.) solution of 4.25 g (12.64 mmol) 4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid ethyl ester in 50 ml of THF. The reaction mixture was stirred 30 min at −50° C. and after letting rise the temperature to RT, for 1 h at RT. The reaction mixture was taken up in ether and washed with 1N HCl and water. The solvent was removed under reduced pressure to give 3.72 g of pure [4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol.

Workup

customto RT
waitfor 1 h at RT
washwashed with 1N HCl and water
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-507331c87d5e41459e6ee1b5fde0e9b2
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06995263B2

Reaction notes

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