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

HRID 2256140Notes

Reaction equation

HRID 2256140 reaction equation
F[C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1.[CH2:20]([N:22](CC)[CH2:23]C)C.Cl.CNC>C(O)(C)C>[CH3:20][N:22]([CH3:23])[C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 5328251N-(3-bromophenyl)-7-fluoropyrido[4,3-d]pyrimidin-4-amine

Product 1

HCID 53282534-N-(3-bromophenyl)-7-N,7-N-dimethylpyrido[4,3-d]pyrimidine-4,7-diamineYield 94%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-fluoro-4-(3-bromoanilino)pyrido[4,3-d]pyrimidine (101 mg, 0.32 mmol), triethylamine (4.4 mL, 32 mmole) and dimethylamine hydrochloride (2.58 g, 32 mmol) in isopropanol (30 mL) contained in a steel bomb is stirred at 100° C. (oil bath) for 4 h. The resulting solution is concentrated under vacuum, basified with aqueous Na2CO3 and diluted with water to give a solid. Filtration and recrystallisation from MeOH/CHCl3 gives 7-dimethylamino-4-(3-bromoanilino)pyrido[4,3-d]pyrimidine (102 mg, 94%) as a pale yellow solid. 1H NMR (DMSO) δ 9.93 (1H, brs), 9.42 (1H, s), 8.48 (1H, s), 8.19 (1H, s), 7.85 (1H, d, J=7.7 Hz), 7.35 (1H, t, J=7.9 Hz), 7.30 (1H, brd, J=7.8 Hz), 6.53 (1H, s), 3.16 (6H, s).

Workup

  1. concentrationThe resulting solution is concentrated under vacuum
  2. additiondiluted with water
  3. customto give a solid
  4. filtrationFiltration and recrystallisation from MeOH/CHCl3

Sources & evidence

ORD record
ord-cdc4e33b2294490c91182c3c3cabe2a1
Source dataset
uspto-grants-1997_08
Patent number
US05654307

Reaction notes

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