2-benzyl-5-(4-(benzyloxy)-3-fluorophenyl)pyrimidin-4(3H)-one → 2-benzyl-5-(3-fluoro-4-hydroxyphenyl)pyrimidin-4(3H)-one

HRID 1676298Notes

Reaction equation

[CH2:1]([C:8]1[NH:13][C:12](=[O:14])[C:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21]CC3C=CC=CC=3)=[C:17]([F:29])[CH:16]=2)=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[CH2:1]([C:8]1[NH:13][C:12](=[O:14])[C:11]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([F:29])[CH:16]=2)=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A suspension of 2-benzyl-5-(4-(benzyloxy)-3-fluorophenyl)pyrimidin-4(3H)-one (0.284 g, 0.735 mmol) in trifluoroacetic acid (3 mL) was stirred at 40° C. for 2 hours and then at room temperature for 16 hours. The reaction mixture was concentrated to dryness and then purified by flash column chromatography, eluting with 20:1 dichloromethane/MeOH. The desired product (0.177 g, 81%) was obtained as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.89 (br s, 1H), 9.98 (s, 1H), 8.08 (s, 1H), 7.58 (dd, J=2.3, 13.3 Hz, 1H), 7.39-7.30 (m, 5H), 7.28-7.22 (m, 1H), 6.96 (dd, J=8.2, 9.4 Hz, 1H), 3.89 (s, 2H). LRMS (ESI pos) m/e 297 (M+1).

Workup

waitat room temperature for 16 hours
concentrationThe reaction mixture was concentrated to dryness
custompurified by flash column chromatography
washeluting with 20:1 dichloromethane/MeOH

Sources & evidence

ORD record: ord-98ae854ac4eb412e92e3e130f5714eb0
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003662B2

Reaction notes

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