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

HRID 522713

반응식

HRID 522713 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-b3a7bc3c52ca414bb9b962cc9b38d56d
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334267B2

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