2-Chloroethyl methyl sulfide → 3-methyl-6-(2-methylsulfanylethyl)-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione

HRID 742969

Reaction equation

HRID 742969 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[CH2:9][NH:10][CH2:11][CH2:12][C:5]=2[NH:4][C:3]1=[O:13].Cl[CH2:15][CH2:16][S:17][CH3:18].[Br-].[Li+].C(N(C(C)C)C(C)C)C>CN(C)C=O>[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[CH2:9][N:10]([CH2:15][CH2:16][S:17][CH3:18])[CH2:11][CH2:12][C:5]=2[NH:4][C:3]1=[O:13]

Participants

6

Reactant 4

HCID 109652-Chloroethyl methyl sulfideHCID 81531DiisopropylethylamineHCID 82050Lithium BromideHCID 102414233-methyl-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione

Product 1

HCID 194233333-methyl-6-(2-methylsulfanylethyl)-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dioneYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

36.3 g of 3-methyl-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]-pyrimidine-2,4-dione, 23 g of 1-chloro-2-methylsulfanylethane (97% pure), 17.4 g of lithium bromide and 27 g of ethyldiisopropylamine in 700 ml of dimethylformamide were stirred for 14 h at 50° C. After the reaction mixture had been concentrated under reduced pressure, the residue was taken up with 400 ml of water and 400 ml, of dichloromethane, the pH was adjusted to 8 with sodium bicarbonate, with stirring, and the mixture was worked up by extraction with dichloromethane and water. 23 g of 3-methyl-6-(2-methylsulfanylethyl)-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione were obtained from the combined dichloromethane phases after drying, concentration and recrystallization of the residue from isopropanol.

Workup

  1. concentrationAfter the reaction mixture had been concentrated under reduced pressure
  2. extractionthe mixture was worked up by extraction with dichloromethane and water

Sources & evidence

ORD record
ord-82a2371955da43e1b96b6c197c37a35c
Source dataset
uspto-grants-1996_09
Patent number
US05556854

Linked notes

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