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

HRID 522713

Reaction equation

HRID 522713 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-b3a7bc3c52ca414bb9b962cc9b38d56d
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Linked notes

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