4-Amino-3-fluorobenzonitrile → (S)-4-(3-(2-Amino-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydropyrimidin-4-yl)-4-fluorophenylamino)-3-fluorobenzonitrile

HRID 2409202Notes

Reaction equation

HRID 2409202 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.[NH2:44][C:45]1[CH:52]=[CH:51][C:48]([C:49]#[N:50])=[CH:47][C:46]=1[F:53]>>[NH2:24][C:25]1[N:30]([CH3:31])[C:29](=[O:32])[C:28]([CH3:33])([CH3:34])[C@:27]([C:36]2[CH:41]=[C:40]([NH:44][C:45]3[CH:52]=[CH:51][C:48]([C:49]#[N:50])=[CH:47][C:46]=3[F:53])[CH:39]=[CH:38][C:37]=2[F:43])([CH3:35])[N:26]=1

Participants

3

Reactant 2

HCID 27564314-Amino-3-fluorobenzonitrileHCID 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 66727455(S)-4-(3-(2-Amino-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydropyrimidin-4-yl)-4-fluorophenylamino)-3-fluorobenzonitrile

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 4-amino-3-fluoro-benzonitrile according to procedure B followed by deprotection yielded the title compound as an off-white foam. MS (ESI): m/z=398.2 [M+H]+.

Sources & evidence

ORD record
ord-d5af1b087bb046b4ac609118d2bfdef5
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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