4-Fluoro-N-methylaniline → HCID 46199899, compound

HRID 1930680Notes

Reaction equation

[F:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.FC(F)(F)S(O[C:16]1[C:17]2[CH2:37][N:36]([C:38](=[O:40])[CH3:39])[CH2:35][CH2:34][C:18]=2[N:19]=[C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[O:33][CH:32]=[N:31][CH:30]=3)=[CH:25][CH:24]=2)[N:21]=1)(=O)=O.S(C1C=CC(C)=CC=1)([O-])(=O)=O>>[F:1][C:2]1[CH:9]=[CH:8][C:5]([N:6]([CH3:7])[C:16]2[C:17]3[CH2:37][N:36]([C:38](=[O:40])[CH3:39])[CH2:35][CH2:34][C:18]=3[N:19]=[C:20]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]4[O:33][CH:32]=[N:31][CH:30]=4)=[CH:25][CH:24]=3)[N:21]=2)=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 680244-Fluoro-N-methylaniline

HCID 85570p-Toluenesulfonate

HCID 593337606-Acetyl-2-(4-(oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl trifluoromethanesulfonate

Product 1

HCID 46199899HCID 46199899, compoundYield 18%

Procedure

1-(4-((4-fluorophenyl)(methyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanone (15 mg, 18%) was prepared from 4-fluoro-N-methylaniline and 6-acetyl-2-(4-(oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl trifluoromethanesulfonate (example 88a) according to the general procedure for amine substitution of tosylate on pyrimidines.

Sources & evidence

ORD record: ord-36061ae5afd946038062c6c9e458be44
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188101B2

Reaction notes

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