Ammonia → 3-Chloro-4-(4-phenylpyrimidin-2-ylamino)benzamide

HRID 40743Notes

Reaction equation

HRID 40743 reaction equation
C[Al](C)C.[NH3:5].O1CCOCC1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[NH:22][C:23]1[N:28]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:26]=[CH:25][N:24]=1)[C:16]([O-])=[O:17]>C(Cl)Cl>[Cl:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[NH:22][C:23]1[N:28]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:26]=[CH:25][N:24]=1)[C:16]([NH2:5])=[O:17]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 16682925TrimethylaluminumHCID 866478723-Chloro-4-(4-phenylpyrimidin-2-ylamino)benzoate

Product 1

HCID 595881623-Chloro-4-(4-phenylpyrimidin-2-ylamino)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethylaluminum (0.8 mL, 2.0 mmol, 2.5M in hexanes) was slowly added to a solution of ammonia in dioxane (4 mL, 0.5 mmol) under argon at room temperature. After stirring for 15 min at room temperature, 3-chloro-4-(4-phenylpyrimidin-2-ylamino)benzoate (0.67 g, 2.0 mmol) in CH2Cl2 was added slowly. The mixture was stirred at room temperature until the ester had been consumed as judged by analytical HPLC analysis. The reaction was quenched with 1 N HCl and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2×), and the combined organics were dried (MgSO4) and concentrated to afford (3-chloro-4-(4-phenylpyrimidin-2-ylamino)benzamide. MS (ESI) 325 (M+H).

Workup

  1. customhad been consumed
  2. customThe reaction was quenched with 1 N HCl
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  5. dry with materialthe combined organics were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1aa9e74c2b4c4620b7384a0544710ff6
Source dataset
uspto-grants-2013_09
Patent number
US08530480B2

Reaction notes

Loading…