Boron tribromide → HCID 67407367, compound

HRID 869289Notes

Reaction equation

C[O:2][C:3]1[C:4](=[O:23])[N:5]([CH3:22])[C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)=[N:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[C:4](=[O:23])[N:5]([CH3:22])[C:6]([C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:13][CH:14]=2)=[N:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 133 g (4.30 mmol) 5-methoxy-3-methyl-2-(4-phenoxyphenyl)pyrimidin-4(3H)-one in 25 ml CH2Cl2 was added 34.4 ml (34.4 mmol) of a 1 M solution of BBr3 in CH2Cl2. The reaction mixture was stirred for 1 h, cooled to 0° C., quenched with 100 ml MeOH, and concentrated in vacuo. Purification by HPLC gave 945 mg (70% yield) of 5-hydroxy-3-methyl-2-(4-phenoxyphenyl)pyrimidin-4(3H)-one. LCMS [M+H]+=2951.

Workup

customquenched with 100 ml MeOH
concentrationconcentrated in vacuo
customPurification by HPLC

Sources & evidence

ORD record: ord-122345fea7cb44729ce29d2070ac08dc
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969364B2

Reaction notes

Loading…