Methylamine → Pd 158780

HRID 50828Notes

Reaction equation

HRID 50828 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]=[C:14](F)[N:13]=[CH:12][C:8]=2[N:9]=[CH:10][N:11]=1.[CH3:20][NH2:21]>C(O)C>[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]=[C:14]([NH:21][CH3:20])[N:13]=[CH:12][C:8]=2[N:9]=[CH:10][N:11]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 5328260N-(3-bromophenyl)-6-fluoropyrido[3,4-d]pyrimidin-4-amine

Product 1

HCID 4707Pd 158780Yield 340%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Treatment of 4-(3-bromoanilino)-6-fluoropyrido[3,4-d]pyrimidine (0.20 g, 0.63 mmol) (see a previous experimental) at 100° C. in a pressure vessel with methylamine in ethanol followed by chromatography on alumina (CH2Cl2/MeOH, 99:1) gives 4-(3-bromoanilino)-6-methylaminopyrido[3,4-d]pyrimidine (0.07 g, 340%). 1H NMR (DMSO) δ 9.69 (1H, s), 8.75 (1H, s), 8.41 (1H, s), 8.21 (1H, brs), 7.93 (1H, brd, J=7.6 Hz), 7.41-7.28 (2H, m), 7.06 (1H, s), 6.82 (1H, q, J=5.0 Hz), 4.95 (3H, d, J=5.0 Hz).

Workup

  1. customat 100° C.

Sources & evidence

ORD record
ord-d48f001c8caf441f9128f8b1590c4ae3
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

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