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

HRID 50839Notes

Reaction equation

HRID 50839 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.Cl.[CH3:21][NH:22][CH3:23].CCN(CC)CC>CCO>[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]([N:22]([CH3:23])[CH3:21])=[N:12][C:8]=2[N:9]=[CH:10][N:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 5328268N-(3-bromophenyl)-7-fluoropyrido[2,3-d]pyrimidin-4-amine

Product 1

HCID 53282704-N-(3-bromophenyl)-7-N,7-N-dimethylpyrido[2,3-d]pyrimidine-4,7-diamineYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Reaction of 4-(3-bromoanilino)-7-fluoropyrido[2,3-d]pyrimidine (see a previous experimental) (0.12 g, 0.38 mmol) with dimethylamine. hydrochloride (92 mg, 1.13 mmol) and Et3N (0.18 mL, 1.32 mmol) in EtOH (15 mL) at 100° C. for 18 h in a pressure vessel, followed by evaporation of the solvent and workup, gives 4-(3-bromoanilino)-7-(dimethylamino)pyrido[2,3-d]pyrimidine (0.11 g, 84%). 1H NMR (DMSO) δ 9.58 (1H, brs), 8.56 (1H, d, J=9.3 Hz) 8.54 (1H, s), 8.18 (1H, t, J=1.9 Hz), 7.84 (dt, Jd=8.0, Hz, J=1.9 Hz), 7.33 (1H, dd, J=8.1, 8.0 Hz) 7.25 (1H, dt, Jd=9.3, Hz, Jt=1.9 Hz), 7.10 (1H, d, J=9.3 Hz), 3.18 (6H, s).

Workup

  1. customat 100° C.
  2. customfor 18 h
  3. customfollowed by evaporation of the solvent and workup

Sources & evidence

ORD record
ord-57f3282ef3044b729ad7928914e0aae2
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

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