Triethylamine → N-(2-methoxy-2-methylpropyl)-6-methyl-2-(methylthio)pyrido[3,4-d]pyrimidin-8-amine

HRID 1480854Notes

Reaction equation

Cl[C:2]1[C:7]2[N:8]=[C:9]([S:12][CH3:13])[N:10]=[CH:11][C:6]=2[CH:5]=[C:4]([CH3:14])[N:3]=1.[CH3:15][O:16][C:17]([CH3:21])([CH3:20])[CH2:18][NH2:19].C(N(CC)CC)C>CN1C(=O)CCC1.CCOC(C)=O>[CH3:15][O:16][C:17]([CH3:21])([CH3:20])[CH2:18][NH:19][C:2]1[C:7]2[N:8]=[C:9]([S:12][CH3:13])[N:10]=[CH:11][C:6]=2[CH:5]=[C:4]([CH3:14])[N:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 8-chloro-6-methyl-2-(methylthio)pyrido[3,4-d]pyrimidine (Preparation 52, 80 mg, 0.354 mmol) in NMP (7 mL) was added 2-methoxy-2-methylpropan-1-amine (0.086 ml, 0.709 mmol) and triethylamine (0.249 mL, 1.772 mmol). The reaction mixture was heated to 120° C. for 18 hours. The reaction mixture was diluted with EtOAc (30 mL), washed with water (30 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 0-50% EtOAc in cyclohexane to afford the title compound (63 mg, 61%).

Workup

washwashed with water (30 mL)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography
washeluting with 0-50% EtOAc in cyclohexane

Sources & evidence

ORD record: ord-a5b01d5798164e9ba9df9a9b89557210
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409907B2

Reaction notes

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