Sodium Chloride → 8-isopropyl-5-methyl-2-methylsulphanyl-8H-pyrido[2,3-d]pyrimidin-7-one
Reaction equation
[H-].[Na+].[CH:3]([NH:6][C:7]1[C:12]([C:13](=O)[CH3:14])=[CH:11][N:10]=[C:9]([S:16][CH3:17])[N:8]=1)([CH3:5])[CH3:4].[Cl-].[Na+].[O:20]1[CH2:25][CH2:24]OCC1>>[CH:3]([N:6]1[C:7]2[N:8]=[C:9]([S:16][CH3:17])[N:10]=[CH:11][C:12]=2[C:13]([CH3:14])=[CH:24][C:25]1=[O:20])([CH3:4])[CH3:5]Participants
Conditions
- Temperature
- 20 °C
Procedure
Sodium hydride (16.75 g, 0.042 mol) is placed in 200 mL dioxane and combined with triethylphosphonoacetate (83.8 mL, 0.419 mmol), so that the temperature does not exceed 5° C. After the addition is complete, the mixture is heated to 20° C. and 1-(4-isopropylamino-2-methylsulphanyl-pyrimidin-5-yl)-ethanone (11.1 g, 0.049 mol) dissolved in 100 mL dioxane is added thereto. The mixture is stirred for 16 h at 90° C., then combined with 10% sodium chloride solution and extracted with ethyl acetate. The organic phase is dried, the solvent is eliminated in vacuo and the crude product is purified by normal phase chromatography (cyclohexane/ethyl acetate 90:10→50:50 in 45 min; flow 200 mL/min) and 8-isopropyl-5-methyl-2-methylsulphanyl-8H-pyrido[2,3-d]pyrimidin-7-one (HPLC-MS: tRet.=1.74 min; MS(M+H)+=250; method FECS1) is obtained.
Workup
- customdoes not exceed 5° C
- additionAfter the addition
- additionis added
- extractionextracted with ethyl acetate
- customThe organic phase is dried
- customthe crude product is purified by normal phase chromatography (cyclohexane/ethyl acetate 90:10→50:50 in 45 min; flow 200 mL/min)
Sources & evidence
- ORD record
- ord-cf67001d168a4aea86c70ac4ca3f66b9
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637549B2
Reaction notes
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