tert-Butyl methyl ether → Ethyl (3-benzyl-2,4-dioxo-2,3,4,5,7,8-hexahydro-1H-pyrido[4,3-d]pyrimidin-6-yl)(2-chlorophenyl)acetate hydrochloride

HRID 742967Notes

Reaction equation

HRID 742967 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[CH2:15][NH:16][CH2:17][CH2:18][C:11]=2[NH:10][C:9]1=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)C(C)C)C.[Cl:29][CH:30]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[Cl:42])[C:31]([O:33][CH2:34][CH3:35])=[O:32].COC(C)(C)C>CN(C)C=O.ClCCl.Cl.CCOCC>[ClH:29].[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[CH2:15][N:16]([CH:30]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[Cl:42])[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:17][CH2:18][C:11]=2[NH:10][C:9]1=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 81531DiisopropylethylamineHCID 13424812Ethyl 2-chloro-2-(2-chlorophenyl)acetateHCID 194233353-benzyl-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione

Product 1

HCID 86749815Ethyl (3-benzyl-2,4-dioxo-2,3,4,5,7,8-hexahydro-1H-pyrido[4,3-d]pyrimidin-6-yl)(2-chlorophenyl)acetate hydrochloride

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 77.2 g of 3-benzyl-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione, 63 g of ethyldiisopropylamine and 126 g of ethyl chloro(2-chlorophenyl)-acetate (89% pure according to GC) in 1700 ml of dimethylformamide was stirred for 48 h at room temperature. It was concentrated under reduced pressure and the residue was worked up by extraction with dichloromethane and water. The dichloromethane phases were combined, dried and concentrated. The residue was diluted with 50 ml of dichloromethane, 1.3 equivalents of a solution of hydrochloric acid in ether were added dropwise at room temperature, with stirring, and 700 ml of tert-butyl methyl ether were added slowly. This initially gave an oil, which solidified gradually to a white mass. This ethyl (3-benzyl-2,4-dioxo-2,3,4,5,7,8-hexahydro-1H-pyrido[4,3-d]pyrimidin-6-yl)(2-chlorophenyl)acetate hydrochloride was purified by recrystallization from dichloromethane/diethyl ether.

Workup

  1. concentrationIt was concentrated under reduced pressure
  2. extractionthe residue was worked up by extraction with dichloromethane and water
  3. customdried
  4. concentrationconcentrated
  5. additionwere added dropwise at room temperature
  6. stirringwith stirring
  7. customThis initially gave an oil, which
  8. customThis ethyl (3-benzyl-2,4-dioxo-2,3,4,5,7,8-hexahydro-1H-pyrido[4,3-d]pyrimidin-6-yl)(2-chlorophenyl)acetate hydrochloride was purified by recrystallization from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-15d2f97e6db841d689be81e9b747957a
Source dataset
uspto-grants-1996_09
Patent number
US05556854

Reaction notes

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