Neopentylamine → 6-methyl-2-(methythio)-N-neopentylpyrido[3,4-d]pyrimidin-8-amine

HRID 1480813Notes

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 8-chloro-6-methyl-2-(methythio)pyrido[3,4-d]pyrimidine (Preparation 52, 128 mg, 0.567 mmol) in NMP (6 mL) was added neopentylamine (0.66 mL, 5.67 mmol). The reaction mixture was heated to 80° C. for 3 hours. The reaction mixture was diluted with EtOAc (30 mL) and water (30 mL), the organic layer was dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 0-50% EtOAc in cyclohexane to give the title compound (38 mg, 24%).

Workup

dry with materialthe organic layer was dried (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-75288c119af6436b8f16aa569c18bb1f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409907B2

Reaction notes

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