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

HRID 400555

Reaction equation

HRID 400555 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4452aeec1e5942ab9541e4e5bce6b96d
Source dataset
uspto-grants-2014_06
Patent number
US08741911B2

Linked notes

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