p-Toluenesulfonic acid → 6-Methyl-2-(methylthio)pyrido[3,4-d]pyrimidin-8(7H)-one

HRID 1480811Notes

Reaction equation

[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]([NH2:11])=[O:10])[C:6]([C:12]#[C:13][CH3:14])=[CH:5][N:4]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:14][C:13]1[NH:11][C:9](=[O:10])[C:7]2[N:8]=[C:3]([S:2][CH3:1])[N:4]=[CH:5][C:6]=2[CH:12]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2-(methylthio)-5-(prop-1-yn-1yl)pyrimidine-4-carboxamide (Preparation 50, 270 mg, 1.303 mmol) in toluene (30 mL) was added pTSA (50 mg, 0.261 mmol). The reaction mixture was heated to 90° C. for 18 hours. The reaction mixture was concentrated in vacuo. The residue was dissolved in NH3 in MeOH (7M, 10 mL) and heated to 80° C. for 18 hours. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography eluting with 0-5% MeOH in DCM to give the title compound (150 mg, 56%).

Workup

concentrationThe reaction mixture was concentrated in vacuo
dissolutionThe residue was dissolved in NH3 in MeOH (7M, 10 mL)
temperatureheated to 80° C. for 18 hours
concentrationThe reaction mixture was concentrated in vacuo
customThe residue was purified by column chromatography
washeluting with 0-5% MeOH in DCM

Sources & evidence

ORD record: ord-2349bc02f8204407b04d14f7270e3508
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409907B2

Reaction notes

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