6-(2,2,2-Trifluoroethoxy)pyridin-3-amine → (S)-2-Amino-6-(2-fluoro-5-(6-(2,2,2-trifluoroethoxy)pyridin-3-ylamino)phenyl)-3,5,5,6-tetramethyl-5,6-dihydropyrimidin-4(3H)-one

HRID 2409228Notes

Reaction equation

HRID 2409228 reaction equation
COC1C=CC(C([NH:24][C:25]2[N:30]([CH3:31])[C:29](=[O:32])[C:28]([CH3:34])([CH3:33])[C@:27]([C:36]3[CH:41]=[C:40](Br)[CH:39]=[CH:38][C:37]=3[F:43])([CH3:35])[N:26]=2)(C2C=CC(OC)=CC=2)C2C=CC=CC=2)=CC=1.[F:44][C:45]([F:56])([F:55])[CH2:46][O:47][C:48]1[N:53]=[CH:52][C:51]([NH2:54])=[CH:50][CH:49]=1>>[NH2:24][C:25]1[N:30]([CH3:31])[C:29](=[O:32])[C:28]([CH3:34])([CH3:33])[C@:27]([C:36]2[CH:41]=[C:40]([NH:54][C:51]3[CH:52]=[N:53][C:48]([O:47][CH2:46][C:45]([F:44])([F:55])[F:56])=[CH:49][CH:50]=3)[CH:39]=[CH:38][C:37]=2[F:43])([CH3:35])[N:26]=1

Participants

3

Reactant 2

HCID 5431566-(2,2,2-Trifluoroethoxy)pyridin-3-amineHCID 57497159(S)-2-{[bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-6-(5-bromo-2-fluoro-phenyl)-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one2×

Product 1

HCID 57497025(S)-2-Amino-6-(2-fluoro-5-(6-(2,2,2-trifluoroethoxy)pyridin-3-ylamino)phenyl)-3,5,5,6-tetramethyl-5,6-dihydropyrimidin-4(3H)-one

Procedure

The coupling of (S)-2-{[bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-6-(5-bromo-2-fluoro-phenyl)-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one (intermediate K) and 6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylamine according to procedure B followed by deprotection yielded the title compound as an off-white foam. MS (ESI): m/z=454.2 [M+H]+.

Sources & evidence

ORD record
ord-ab45c2bf297b4d7a83b4276dc7bba26d
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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