P-Anisidine → 4-N-(4-methoxyphenyl)pyrido[4,3-d]pyrimidine-4,7-diamine

HRID 50852Notes

Reaction equation

HRID 50852 reaction equation
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8](SC)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1.[CH3:14][O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1>C(O)C>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:20][C:19]3[CH:21]=[CH:22][C:16]([O:15][CH3:14])=[CH:17][CH:18]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 53280624-N-(4-methoxyphenyl)pyrido[4,3-d]pyrimidine-4,7-diamineYield 25%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (129 mg, 0.62 mmol) and 4-methoxyaniline ((0.15 g, 1.2 mmol) was in ethanol (5 mL) was heated at 40° C. for 16 h, and then reflux for 3 h. The reaction mixture was cooled to 0° C. overnignt, and the solid was colected by vacuum filtration and recrystalized from isopropanol to give 7-amino-4-(4-methoxyanilino)pyrido[4,3-d]pyrimidine (42 mg, 25%) as a yellow solid. 1H NMR (DMSO) δ 10.00 (1H, brs), 9.31 (1H, s), 8.35 (1H, s), 7.62 (2H, d, J=9.2 Hz), 6.96 (2H, d, J=9.2 Hz), 6.70 (2H, slbrs), 6.41 (1H, s), 3.77 (3H, s).

Workup

  1. temperaturereflux for 3 h
  2. temperatureThe reaction mixture was cooled to 0° C. overnignt
  3. filtrationthe solid was colected by vacuum filtration
  4. customrecrystalized from isopropanol

Sources & evidence

ORD record
ord-0e23e24b350049ec97d01f3e8aad66fa
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

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