4-Chloro-5-methyl-o-anisidine → (S)-2-Amino-6-(5-(4-chloro-2-methoxy-5-methylphenylamino)-2-fluorophenyl)-3,5,5,6-tetramethyl-5,6-dihydropyrimidin-4(3H)-one

HRID 2409204Notes

Reaction equation

HRID 2409204 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.[Cl:44][C:45]1[C:50]([CH3:51])=[CH:49][C:48]([NH2:52])=[C:47]([O:53][CH3:54])[CH:46]=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:52][C:48]3[CH:49]=[C:50]([CH3:51])[C:45]([Cl:44])=[CH:46][C:47]=3[O:53][CH3:54])[CH:39]=[CH:38][C:37]=2[F:43])([CH3:35])[N:26]=1

Participants

3

Reactant 2

HCID 807824-Chloro-5-methyl-o-anisidineHCID 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 57497042(S)-2-Amino-6-(5-(4-chloro-2-methoxy-5-methylphenylamino)-2-fluorophenyl)-3,5,5,6-tetramethyl-5,6-dihydropyrimidin-4(3H)-one

Procedure

The coupling (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 4-chloro-2-methoxy-5-methyl-phenylamine according to procedure B followed by deprotection yielded the title compound as an off-white solid. MS (ESI): m/z=433.3 [M+H]+.

Sources & evidence

ORD record
ord-5beb18ad8af245628a314fefd2d66eb6
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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