Aniline → HCID 5328051, compound

HRID 1386153Notes

Reaction equation

HRID 1386153 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.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 5328051HCID 5328051, compoundYield 51%

Conditions

Temperature
180 °C

Procedure

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (0.136 g, 0.7 mmol) and aniline (0.5 mL, 5.5 mmol) is refluxed under N2 at 180° C. for 2 h. The reaction mixture is cooled to 25° C., when it precipitates. The solid is collected by suction filtration and recrystallized from isopropanol, and dried in a vacuum oven overnight. 7-Amino-4-anilinopyrido[4,3-d]pyrimidine (84 mg, 51%) is isolated as a light yellow solid. 1H NMR (DMSO) δ 9.82 (1H, s), 9.34 (1H, s), 8.37 (1H, s), 7.80 (2H, d, J=7.5 Hz), 7.38 (2H, t, J=7.5 Hz), 7.12 (1H, t, J=7.5 Hz), 6.61 (2H, brs) 6.43 (1H, s).

Workup

  1. temperatureThe reaction mixture is cooled to 25° C.
  2. customwhen it precipitates
  3. filtrationThe solid is collected by suction filtration
  4. customrecrystallized from isopropanol
  5. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-cf101ed9f62d45b48c45e1190a825500
Source dataset
uspto-grants-2001_07
Patent number
US06265410B1

Reaction notes

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