(S)-2-amino-6-(5-amino-2-fluoro-phenyl)-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one → (6S)-2-amino-6-(5-(3-chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ylamino)-2-fluorophenyl)-3,5,5,6-tetramethyl-5,6-dihydropyrimidin-4(3H)-one

HRID 2409154Notes

Reaction equation

HRID 2409154 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:23]=[N:24][C:25]2[C:30](=O)[CH2:29][CH2:28][C:26]=2[CH:27]=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:30]3[C:25]4=[N:24][CH:23]=[C:22]([Cl:21])[CH:27]=[C:26]4[CH2:28][CH2:29]3)[CH:16]=[CH:15][C:14]=2[F:20])([CH3:12])[N:3]=1

Participants

4

Reactant 3

HCID 57497157(S)-2-amino-6-(5-amino-2-fluoro-phenyl)-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one2×HCID 58082858HCID 58082858, compoundHCID 178419135HCID 178419135, compound

Product 1

HCID 56654776(6S)-2-amino-6-(5-(3-chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ylamino)-2-fluorophenyl)-3,5,5,6-tetramethyl-5,6-dihydropyrimidin-4(3H)-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 3-chloro-5H-cyclopentapyridin-7(6H)-one using decaborane yielded (6S)-2-amino-6-(5-(3-chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ylamino)-2-fluorophenyl)-3,5,5,6-tetramethyl-5,6-dihydropyrimidin-4(3H)-one as a white foam. MS (ESI): m/z=430.3 [M+H]+.

Sources & evidence

ORD record
ord-7d85bfc46f214c6d90c338d110c91295
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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