Aniline → Pyrido[4,3-d]pyrimidin-4-amine,n-phenyl-

HRID 1059564Notes

Reaction equation

HRID 1059564 reaction equation
CS[C:3]1[C:4]2[CH:12]=[N:11][CH:10]=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCO>[NH:13]([C:3]1[C:4]2[CH:12]=[N:11][CH:10]=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 106548874-Methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 54457063Pyrido[4,3-d]pyrimidin-4-amine,n-phenyl-Yield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-methylthiopyrido[4,3-d]pyrimidine (174 mg, 0.97 mmol), and aniline (186.2 mg, 1.99 mmol) in EtOH (2 mL) is refluxed under N2 for 12 h. Cooling to 0° C. forms a solid which is filtered to yield 4-anilinopyrido-[4,3-d]pyrimidine (34.5 mg, 16%). 1H NMR (DMSO) δ 10.29 (1H, brs), 9.86 (1H, s), 8.82 (1H, d, J=5.8 Hz), 8.72 (1H, s), 7.85 (2H, d, J=7.5 Hz), 7.66 (1H, d, J=5.5 Hz), 7.45 (2H, t, J=8.0 Hz), 7.23 (1H, t, J=7.3 Hz).

Workup

  1. temperatureis refluxed under N2 for 12 h
  2. filtrationis filtered

Sources & evidence

ORD record
ord-ce2c1aca87d54b12945e0655c937c774
Source dataset
uspto-grants-2003_02
Patent number
US06521620B1

Reaction notes

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