Ammonia → 4-N-(3-bromophenyl)pyrido[2,3-d]pyrimidine-4,7-diamine

HRID 50837Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[NH:5][C:6]1[C:7]2[CH:15]=[CH:14][C:13](F)=[N:12][C:8]=2[N:9]=[CH:10][N:11]=1.[NH3:20]>CCO>[NH2:20][C:13]1[CH:14]=[CH:15][C:7]2[C:6]([NH:5][C:4]3[CH:17]=[CH:18][CH:19]=[C:2]([Br:1])[CH:3]=3)=[N:11][CH:10]=[N:9][C:8]=2[N:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 4-(3-bromoanilino)-7-fluoropyrido[2,3-d]pyrimidine (0.20 g, 0.63 mmol) in EtOH (20 mL) is saturated with ammonia and warmed at 100° C. in a pressure vessel for 30 h. The solvent is removed under reduced pressure to give 7-amino-4-(3-bromoanilino)pyrido[2,3-d]pyrimidine (0.18 g, 90%). 1H NMR (DMSO) δ 9.97 (1H, brs), 8.59 (1H, s), 8.51 (1H, d, J=9.3 Hz), 8.11 (1H, sl brs), 7.77 (1H, brd, J=6.3 Hz), 7.44 (2H, brs), 7.37-7.30 (2H, m), 6.81 (1H, d, J=9.3 Hz).

Workup

customThe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-a93115e1909d40c3965843845a5a529f
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713484B2

Reaction notes

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