3-Bromoaniline → N-(3-bromophenyl)-6-fluoropyrido[3,4-d]pyrimidin-4-amine

HRID 1386199Notes

Reaction equation

HRID 1386199 reaction equation
[F:1][C:2]1[N:12]=[CH:11][C:5]2[N:6]=[CH:7][NH:8][C:9](=O)[C:4]=2[CH:3]=1.O=P(Cl)(Cl)Cl.[Br:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22]>>[Br:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH:22][C:9]1[C:4]2[CH:3]=[C:2]([F:1])[N:12]=[CH:11][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

4

Reactant 3

HCID 115623-BromoanilineHCID 24813Phosphorus oxychlorideHCID 1354173706-fluoropyrido[3,4-d]pyrimidin-4-ol

Product 1

HCID 5328260N-(3-bromophenyl)-6-fluoropyrido[3,4-d]pyrimidin-4-amineYield 63%

Procedure

Reaction of 6-fluoro-3H-pyrido[3,4-d]pyrimidin-4-one (0.60 g, 3.6 mmol) with POCl3, followed by reaction of the crude 4,6-dihalo compound with 3-bromoaniline gives 4-(3-bromoanilino)-6-fluoropyrido[3,4-d]pyrimidine (0.73 g, 63%). 1H NMR (DMSO) δ 10.09 (1H, brs), 8.96 (1H, s), 8.75 (1H, s), 8.25 (2H, m), 7.90 (1H, brd, J=6.5 Hz), 7.44-7.34 (2H, m).

Sources & evidence

ORD record
ord-32e63e597b874509b8eb098fc4e150b8
Source dataset
uspto-grants-2001_07
Patent number
US06265410B1

Reaction notes

Loading…