Acetone → 7-Methyl-2-(methylthio)pyrido[2,3-d]pyrimidine

HRID 400555

반응식

HRID 400555 반응식
[NH2:1][C:2]1[C:7]([CH:8]=O)=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.[OH-].[K+].[CH3:14][C:15]([CH3:17])=O>>[CH3:17][C:15]1[CH:14]=[CH:8][C:7]2[CH:6]=[N:5][C:4]([S:10][CH3:11])=[N:3][C:2]=2[N:1]=1

참가 물질

4

반응물 3

HCID 180AcetoneHCID 14797Potassium HydroxideHCID 2957694-Amino-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

생성물 1

HCID 866970117-Methyl-2-(methylthio)pyrido[2,3-d]pyrimidine

실험 절차

Treat a solution of 4-amino-2-(methylthio)pyrimidine-5-carbaldehyde (10 g, 59.1 mmol) in acetone (100 mL) with KOH (3.32 g, 59.1 mmol), stir at RT for 10 min, then concentrate to dryness. Treat the residue with EtOAc, wash with saturated. aqueous NaHCO3, then brine, dry over Na2SO4 and concentrate to obtain 7-methyl-2-(methylthio)pyrido[2,3-d]pyrimidine. MS (m/z): 192.1 (M+1). Add a solution of methylamine in ethanol (33%, 80 mL) and heat at 110° C. overnight in a pressure tube. Remove the solvent under reduced pressure and purify the crude product by silica gel chromatography (50-100% EtOAc/Hexanes) to obtain the title compound (6.73 g, 65%, over two steps). MS (m/z): 175.1 (M+1).

후처리

  1. concentrationconcentrate to dryness
  2. additionTreat the residue with EtOAc
  3. washwash with saturated
  4. dry with materialaqueous NaHCO3, then brine, dry over Na2SO4
  5. concentrationconcentrate

출처 및 근거

ORD 기록
ord-4452aeec1e5942ab9541e4e5bce6b96d
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741911B2

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