3-Bromoaniline → N-(3-bromophenyl)pyrido[2,3-d]pyrimidin-4-amine

HRID 50832Notes

Reaction equation

HRID 50832 reaction equation
CS[C:3]1[C:4]2[CH:12]=[CH:11][CH:10]=[N:9][C:5]=2[N:6]=[CH:7][N:8]=1.[Br:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17]>>[Br:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH:17][C:3]1[C:4]2[CH:12]=[CH:11][CH:10]=[N:9][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

3

Reactant 2

HCID 115623-BromoanilineHCID 232404674-Methylthiopyrido[2,3-d]pyrimidine

Product 1

HCID 5328266N-(3-bromophenyl)pyrido[2,3-d]pyrimidin-4-amine

Conditions

Temperature
100 °C

Procedure

A mixture of 4-methylthiopyrido[2,3-d]pyrimidine (157 mg, 0.89 mmol, and 3-bromoaniline (1 mL) is heated to 100° C. for 2 h. On cooling a precipitate forms which is filtered then washed with EtOH and air dried to yield 4-(3-bromoanilino)pyrido[2,3-d]pyrimidine (55.5 mg, 20%. 1H NMR (DMSO) δ 10.13 (1H, s), 9.11 (1H, dd, J=1.7, 4.3 Hz), 9.01 (1H, dd, J=1.7, 8.2 Hz), 8.81 (1H, s), 8.22 (1H, s), 7.90 (1H, d, J=7.7 Hz), 7.71 (1H, dd, J=4.3, 8.0 Hz), 7.40 (2H, m).

Workup

  1. temperatureOn cooling a precipitate forms which
  2. filtrationis filtered
  3. washthen washed with EtOH and air
  4. customdried

Sources & evidence

ORD record
ord-35eecb928ef846feb8b6af6fe64cbfad
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

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