Sodium borohydride → 2-(4-(Trifluoromethoxy)phenyl)pyrimidine-5-methanol

HRID 1496914Notes

Reaction equation

[BH4-].[Na+].[F:3][C:4]([F:21])([F:20])[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]=[CH:16][C:15]([CH:18]=[O:19])=[CH:14][N:13]=2)=[CH:8][CH:7]=1>CO>[F:21][C:4]([F:3])([F:20])[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[CH:14][C:15]([CH2:18][OH:19])=[CH:16][N:17]=2)=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

NaBH4 (0.22 g, 5.82 mmol) was added to a solution of aldehyde 90 (0.776 g, 2.89 mmol) in MeOH (100 mL) at 0° C. The solution was stirred at 0° C. for 1 h, then quenched with brine and partitioned between EtOAc and water. Column chromatography of the organic portion on silica gel (eluting with 1:1 EtOAc/hexanes) gave {2-[4-(trifluoromethoxy)phenyl]-5-pyrimidinyl}methanol (91) (0.657 g, 84%) as a white solid: mp 84-85° C.; 1H NMR [(CD3)2SO] δ 8.86 (s, 2H), 8.50 (d, J=8.9 Hz, 2H), 7.51 (d, J=8.9 Hz, 2H), 5.46 (t, J=5.5 Hz, 1H), 4.60 (d, J=5.5 Hz, 2H). APCI MS m/z 271 [M+H]+.

Workup

customquenched with brine
custompartitioned between EtOAc and water

Sources & evidence

ORD record: ord-cebb486e7858427592fc66ec745ee48c
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09198913B2

Reaction notes

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