Acetic Anhydride → HCID 67388180, compound

HRID 269839Notes

Reaction equation

HRID 269839 reaction equation
C[N:2]1[C:6](=[O:7])[CH2:5][CH2:4][CH2:3]1.Cl.Cl.NCC1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[N:24]=[C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=3)[C:22]([C:33]([NH2:35])=[O:34])=[CH:21][N:20]=2)=[CH:14][CH:13]=1.C(N(CC)CC)C.C(OC(=O)C)(=O)C>O>[C:6]([NH:2][CH2:3][C:4]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[N:24]=[C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=3)[C:22]([C:33]([NH2:35])=[O:34])=[CH:21][N:20]=2)=[CH:14][CH:13]=1)(=[O:7])[CH3:5]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 67388260HCID 67388260, compound

Product 1

HCID 67388180HCID 67388180, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 10 ml portion of NMP solution containing 500 mg of 2-{[4-(aminomethyl)phenyl]amino}-4-[(3-methylphenyl)amino]pyrimidine-5-carboxamide dihydrochloride synthesized by the method described in Example 8 of WO 99/31073 was mixed with 0.53 ml of triethylamine and 0.12 ml of acetic anhydride, followed by stirring overnight at room temperature. The reaction mixture was mixed with water and extracted with ethyl acetate, the organic layer was washed with saturated brine and then the solvent was evaporated. The resulting residue was triturated with methanol, and washed to obtain 270 mg of 2-({4-[(acetylamino)methyl]phenyl}amino)-4-[(3-methylphenyl)amino]pyrimidine-5-carboxamide as a pale yellow solid.

Workup

  1. customsynthesized by the method
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. customthe solvent was evaporated
  5. customThe resulting residue was triturated with methanol
  6. washwashed

Sources & evidence

ORD record
ord-ae12230e1e82443f8d6983e2611d0a2c
Source dataset
uspto-grants-2008_11
Patent number
US07449456B2

Reaction notes

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