2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-amine → (S)-2-Amino-6-(5-(2,2-dimethyl-2,3-dihydrobenzofuran-7-ylamino)-2-fluorophenyl)-3,5,5,6-tetramethyl-5,6-dihydropyrimidin-4(3H)-one

HRID 2409206Notes

Reaction equation

HRID 2409206 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.[CH3:44][C:45]1([CH3:55])[CH2:49][C:48]2[CH:50]=[CH:51][CH:52]=[C:53]([NH2:54])[C:47]=2[O:46]1>>[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:54][C:53]3[C:47]4[O:46][C:45]([CH3:55])([CH3:44])[CH2:49][C:48]=4[CH:50]=[CH:51][CH:52]=3)[CH:39]=[CH:38][C:37]=2[F:43])([CH3:35])[N:26]=1

Participants

3

Reactant 2

HCID 916972,2-Dimethyl-2,3-dihydro-1-benzofuran-7-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 57497037(S)-2-Amino-6-(5-(2,2-dimethyl-2,3-dihydrobenzofuran-7-ylamino)-2-fluorophenyl)-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 2,2-dimethyl-2,3-dihydro-benzofuran-7-ylamine according to procedure B followed by deprotection yielded the title compound as an off-white solid. MS (ESI): m/z=425.2 [M+H]+.

Sources & evidence

ORD record
ord-110f01e6741c447cb147a326dbd8f979
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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