2-bromo-1-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)ethanone hydrobromide → (8S)-2-chloro-9-[2-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-2-oxoethyl]-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one

HRID 633725Notes

Reaction equation

HRID 633725 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[NH:12][C@H:11]([C:13]([F:16])([F:15])[F:14])[CH2:10][CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1.Br.Br[CH2:19][C:20]([C:22]1[CH:31]=[N:30][C:29]2[NH:28][CH2:27][CH2:26][O:25][C:24]=2[CH:23]=1)=[O:21]>>[Cl:1][C:2]1[N:3]=[C:4]2[N:12]([CH2:19][C:20]([C:22]3[CH:31]=[N:30][C:29]4[NH:28][CH2:27][CH2:26][O:25][C:24]=4[CH:23]=3)=[O:21])[C@H:11]([C:13]([F:14])([F:15])[F:16])[CH2:10][CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1

Participants

3

Reactant 2

HCID 1181943912-bromo-1-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)ethanone hydrobromideHCID 136238740(S)-8-chloro-2-(trifluoromethyl)-3,4-dihydro-1H-pyrimido[1,2-a]pyrimidin-6(2H)-one

Product 1

HCID 118194446(8S)-2-chloro-9-[2-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-2-oxoethyl]-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one

Procedure

200 mg (0.79 mmol) of (8S)-2-chloro-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 319.86 mg (0.95 mmol) of 2-bromo-1-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)ethanone hydrobromide were used in the reaction. After purification by chromatography on silica gel (eluent: 90/10 DCM/MeOH), 110 mg of (8S)-2-chloro-9-[2-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-2-oxoethyl]-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one are obtained, the characteristics of which are as follows:

Workup

  1. customAfter purification by chromatography on silica gel (eluent: 90/10 DCM/MeOH), 110 mg of (8S)-2-chloro-9-[2-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-2-oxoethyl]-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one
  2. customare obtained

Sources & evidence

ORD record
ord-1ba9004e35e646dbbac2274a7a20b390
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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