6-Chloro-3-Benzofuranone → (S)-2-Amino-6-[5-(6-chloro-2,3-dihydro-benzofuran-3-ylamino)-2-fluoro-phenyl]-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one

HRID 2409192Notes

Reaction equation

HRID 2409192 reaction equation
[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([CH3:11])([CH3:10])[C@:4]([C:13]2[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][C:14]=2[F:20])([CH3:12])[N:3]=1.[Cl:21][C:22]1[CH:31]=[CH:30][C:25]2[C:26](=O)[CH2:27][O:28][C:24]=2[CH:23]=1.[B][B][B][B][B][B][B][B][B][B]>>[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([CH3:10])([CH3:11])[C@:4]([C:13]2[CH:18]=[C:17]([NH:19][CH:26]3[C:25]4[CH:30]=[CH:31][C:22]([Cl:21])=[CH:23][C:24]=4[O:28][CH2:27]3)[CH:16]=[CH:15][C:14]=2[F:20])([CH3:12])[N:3]=1

Participants

4

Reactant 3

HCID 137781336-Chloro-3-BenzofuranoneHCID 57497157HCID 57497157, compound2×HCID 178419135HCID 178419135, compound

Product 1

HCID 57497073(S)-2-Amino-6-[5-(6-chloro-2,3-dihydro-benzofuran-3-ylamino)-2-fluoro-phenyl]-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one

Procedure

The reductive amination of (S)-2-amino-6-(5-amino-2-fluoro-phenyl)-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one (intermediate J) and 6-chloro-benzofuran-3-one using decaborane yielded a mixture of epimers of the title compound as a white foam. MS (ESI): m/z=431.3 [M+H]+.

Workup

  1. customyielded

Sources & evidence

ORD record
ord-22160a3c4db24a76bf500a9ceafd24c4
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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