Aniline → 7-(3-Chloropyridin-2-yl)-N-(phenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine

HRID 971219Notes

Reaction equation

Cl[C:2]1[C:3]2[CH2:11][CH2:10][N:9]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][N:13]=3)[CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C>[Cl:18][C:17]1[C:12]([N:9]2[CH2:10][CH2:11][C:3]3[C:2]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[N:7][CH:6]=[N:5][C:4]=3[CH2:8]2)=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 180 °C

Procedure

4-Chloro-7-(3-chloro-pyridin-2-yl)-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidine (150 mg, 0.54 mmol) was dissolved in acetonitrile (2 mL). To the mixture was added aniline (60 mg). The mixture was heated in a sealed tube at 180° C. for 30 minutes in a Personal Chemistry Microwave (Smith Creator). The solvent was removed under vacuum and the resulting orange residue was purified by flash chromatography over silica gel using a 0-100% ethyl acetate-hexane gradient to give the product as an off white solid (60 mg).

Workup

customThe solvent was removed under vacuum
customthe resulting orange residue was purified by flash chromatography over silica gel using a 0-100% ethyl acetate-hexane gradient

Sources & evidence

ORD record: ord-516e1152c3be4900a1b97a1d5f54389c
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312330B2

Reaction notes

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