Ammonia → 4-N-(3-bromophenyl)pyrido[3,2-d]pyrimidine-4,6-diamine

HRID 50770Notes

Reaction equation

HRID 50770 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[N:15]=[C:14](F)[CH:13]=[CH:12][C:8]=2[N:9]=[CH:10][N:11]=1.[NH3:20]>C(O)C>[NH2:20][C:14]1[CH:13]=[CH:12][C:8]2[N:9]=[CH:10][N:11]=[C:6]([NH:5][C:4]3[CH:17]=[CH:18][CH:19]=[C:2]([Br:1])[CH:3]=3)[C:7]=2[N:15]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 5328276N-(3-bromophenyl)-6-fluoropyrido[3,2-d]pyrimidin-4-amine

Product 1

HCID 53282744-N-(3-bromophenyl)pyrido[3,2-d]pyrimidine-4,6-diamineYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Reaction of 4-(3-bromoanilino)-6-fluoropyrido[3,2-d]pyrimidine (0.12 g, 0.38 mmol)(described in a previous experimental) with a saturated solution of ammonia in ethanol in a pressure vessel at 100° C. for 18 h gives 6-amino-4-(3-bromoanilino)pyrido[3,2-d]pyrimidine, (87 mg, 72%). 1H NMR (CDCl3) δ 8.76 (1H, brs), 8.64 (1H, s), 8.23 (1H, brs), 7.93 (1H, d, J=9.0 Hz), 7.81 (1H, dt, Jd=7.7 Hz, Jt=1.8 Hz), 7.28-7.22 (2H, m), 7.00 (1H, d, J=9.0 Hz), 4.90 (2H, brs).

Workup

  1. customat 100° C.
  2. customfor 18 h

Sources & evidence

ORD record
ord-e88951139c984b8eba2ef2e1ff660882
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

Loading…