Trifluoroacetic acid → 6-fluoro-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one

HRID 1749094Notes

Reaction equation

HRID 1749094 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:7](=[O:21])[N:8](CC3C=CC(OC)=CC=3)[CH2:9][C:10]=2[N:11]=1.C(O)(C(F)(F)F)=O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:7](=[O:21])[NH:8][CH2:9][C:10]=2[N:11]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 709803326-fluoro-3-(4-methoxy-benzyl)-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one

Product 1

HCID 709815066-fluoro-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-oneYield 59.4%

Procedure

6-Fluoro-3-(4-methoxy-benzyl)-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one (300 mg, 0.83 mmol) was deprotected according to the method of General procedure 1 (TFA deprotection). The free base was isolated and purified by column chromatography (SiO2, eluted with petrol—EtOAc 0-100%) to afford 6-fluoro-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one (120 mg). MS: [M+H]+=244.

Workup

  1. customThe free base was isolated
  2. custompurified by column chromatography (SiO2, eluted with petrol—EtOAc 0-100%)

Sources & evidence

ORD record
ord-f3fb3e652b4c447eab8e1d6c23dfa9f8
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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