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

HRID 50771Notes

Reaction equation

HRID 50771 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.Cl.CN.[CH2:23]([N:25](CC)CC)C>C(O)C>[CH3:23][NH:25][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

5

Reactant 3

HCID 8471TriethylamineHCID 5328276N-(3-bromophenyl)-6-fluoropyrido[3,2-d]pyrimidin-4-amineHCID 6364545Methylamine hydrochloride

Product 1

HCID 53282774-N-(3-bromophenyl)-6-N-methylpyrido[3,2-d]pyrimidine-4,6-diamineYield 81.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Reaction of 4-(3-bromoanilino)-6-fluoropyrido[3,2-d]pyrimidine (50 mg, 0.16 mmol)(described in a previous experimental) with methylamine hydrochloride (32 mg, 0.47 mmol) and triethylamine (70 μL, 0.55 mmol) in ethanol (10 mL) in a pressure vessel at 100° C. for 18 h gives 6-methylamino-4-(3-bromoanilino)pyrido[3,2-d]pyrimidine (43 mg, 81%). 1H NMR (CDCl3) δ 8.81. (1H, brs), 8.61 (1H, s), 8.19 (1H, t, J=1.8 Hz), 7.86 (1H, d, J=9.1 Hz,), 7.83 (1H, dt, Jd=7.7 Hz, Jt=1.8 Hz), 7.28-7.21 (2H, m), 6.92 (1H, d, J=9.1 Hz), 4.97 (1H, q, J=5.0 Hz), 3.13 (3H, d, J=5.0 Hz)

Workup

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

Sources & evidence

ORD record
ord-2f78d167996a49c098eadef6d821b513
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

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