Aniline → HCID 10262963, compound

HRID 2256158Notes

Reaction equation

HRID 2256158 reaction equation
CS[C:3]1[C:4]2[CH:12]=[CH:11][N: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>>[NH:13]([C:3]1[C:4]2[CH:12]=[CH:11][N: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

3

Reactant 2

HCID 6115AnilineHCID 232404654-Methylthiopyrido[3,4-d]pyrimidine

Product 1

HCID 10262963HCID 10262963, compoundYield 23%

Conditions

Temperature
100 °C

Procedure

A mixture of 4-methylthiopyrido[3,4-d]pyrimidine (75 mg, 0.42 mmol), and aniline (1 mL) is heated to 100° C. under N2 for 2 h. The reaction mixture is then chromatographed on silica using MPLC and eluting with a gradient system (CHCl3 to 5% MeOH in CHCl3). The fractions are concentrated under reduced pressure, and the resulting solid is recrystallized from Et2O to yield 4-anilinopyrido[3,4-d]pyrimidine (21.2 mg, 23%) as a yellow solid. 1H NMR (DMSO) 8 10.09 (1H, s), 9.18 (1H, s), 8.74 (1H, d, J=5.3 Hz), 8.46 (1H, d, J=5.8 Hz), 7.89 (2H, d, J=8.5 Hz), 7.45 (2H, t, J=7.9 Hz), 7.21 (1H, t, J=7.4 Hz).

Workup

  1. customThe reaction mixture is then chromatographed on silica using MPLC
  2. washeluting with a gradient system (CHCl3 to 5% MeOH in CHCl3)
  3. concentrationThe fractions are concentrated under reduced pressure
  4. customthe resulting solid is recrystallized from Et2O

Sources & evidence

ORD record
ord-8f2585cdae374a5a944f99c3a6ac02f7
Source dataset
uspto-grants-1997_08
Patent number
US05654307

Reaction notes

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