Pyridine → 4-(6-Chloro-2,3dihydro-indol-1-yl)-pyrido[3,4-d]pyrimidine

HRID 1937389Notes

Reaction equation

Cl[C:2]1[C:3]2[CH:11]=[CH:10][N:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:12][C:13]1[CH:21]=[C:20]2[C:16]([CH2:17][CH2:18][NH:19]2)=[CH:15][CH:14]=1.N1C=CC=CC=1.C(Cl)Cl>CN(C=O)C>[Cl:12][C:13]1[CH:21]=[C:20]2[C:16]([CH2:17][CH2:18][N:19]2[C:2]2[C:3]3[CH:11]=[CH:10][N:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 70 °C

Procedure

4-Chloropyrido[3,4-d]pyrimidine (0.10 g, 0.60 mmol), 6-chloroindoline (0.10 g, 0.66 mmol) and pyridine (0.14 g, 1.81 mmol) were combined in DMF (1 mL) and heated at 70° C. for 3 hours. The reaction was cooled to room temperature and then added to methylene chloride (150 mL). The organic layer was washed with saturated sodium carbonate and water and then dried over sodium sulfate. The solvent was removed by rotary evaporation and the residue purified by column chromatography (silica gel, 9/2/1—CH2Cl2/hexanes/methanol) to give the title product as a pale yellow residue (0.048 g, 28%). MP 194-6° C.; LCMS: 283 (MH+).

Workup

temperatureThe reaction was cooled to room temperature
washThe organic layer was washed with saturated sodium carbonate and water
dry with materialdried over sodium sulfate
customThe solvent was removed by rotary evaporation
customthe residue purified by column chromatography (silica gel, 9/2/1—CH2Cl2/hexanes/methanol)

Sources & evidence

ORD record: ord-7b22fd35f8484baf9bd82b82be07c575
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06395733B1

Reaction notes

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