Methyl 4-bromo-3-methylbutanoate → 5-(3-Fluorophenyl)-10-hydroxy-1,3,9-trimethyl-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione

HRID 2201305Notes

Reaction equation

HRID 2201305 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]3[C:11]([CH:12]([OH:18])[CH2:13][CH:14](C)[CH2:15]3)=[C:10]3[N:19]([CH3:26])[C:20](=[O:25])[N:21]([CH3:24])[C:22](=[O:23])[C:9]=23)[CH:5]=[CH:6][CH:7]=1.Br[CH2:28]C(C)CC(OC)=O.S[C@@H](C)CN1C(C2C=CC=CC=2)=C2C(N(C)C(=O)N(C)C2=O)=C1>>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]3[C:11]([CH:12]([OH:18])[CH:13]([CH3:28])[CH2:14][CH2:15]3)=[C:10]3[N:19]([CH3:26])[C:20](=[O:25])[N:21]([CH3:24])[C:22](=[O:23])[C:9]=23)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 14104192Methyl 4-bromo-3-methylbutanoateHCID 86723519(S)-6-(2-Mercaptopropyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione2×HCID 867235355-(3-Fluorophenyl)-10-hydroxy-1,3,8-trimethyl-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione

Product 1

HCID 867235365-(3-Fluorophenyl)-10-hydroxy-1,3,9-trimethyl-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione

Procedure

The title compound was prepared analogously to 5-(3-fluorophenyl)-10-hydroxy-1,3,8-trimethyl-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione (Intermediate La) by replacing Methyl 4-bromo-3-methylbutanoate (Intermediate T) with methyl 4-bromo-2-methylbutanoate (Intermediate S).

Sources & evidence

ORD record
ord-a0fb461d38204157868060282ddc2790
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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