Ammonia → 2-(Methylthio)pyrido[3,4-d]pyrimidin-8(7H)-one

HRID 1480804Notes

Reaction equation

HRID 1480804 reaction equation
C(O/[CH:4]=[CH:5]/[C:6]1[C:7]([C:14]([O:16]C)=O)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)C.[NH3:18]>CO.C1(C)C=CC=CC=1>[CH3:13][S:12][C:9]1[N:10]=[CH:11][C:6]2[CH:5]=[CH:4][NH:18][C:14](=[O:16])[C:7]=2[N:8]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 89996170(E)-methyl 5-(2-ethoxyvinyl)-2-(methylthio)pyrimidine-4-carboxylate

Product 1

HCID 899959692-(Methylthio)pyrido[3,4-d]pyrimidin-8(7H)-oneYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

(E)-Methyl 5-(2-ethoxyvinyl)-2-(methylthio)pyrimidine-4-carboxylate (Preparation 31, 2.30 g, 9.04 mmol) was treated with ammonia in methanol 7M (45 mL) and heated to 85° C. for 18 hours in a capped vial. The solvent was removed under reduced pressure, and the resulting solid was treated with TsOH monohydrate (175 mg, 0.92 mmol), suspended in toluene (50 mL) and heated to 90° C. for 2 hours. The mixture was concentrated and the residue was purified by silica gel column chromatography eluting with 0 to 5% MeOH in DCM to give the title compound (1.47 g, 84%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. temperatureheated to 90° C. for 2 hours
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified by silica gel column chromatography
  5. washeluting with 0 to 5% MeOH in DCM

Sources & evidence

ORD record
ord-01f2ee29643a4ce9a6e231b42e3a3f5a
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

Loading…