Sodium Hydroxide → HCID 22273502, compound

HRID 1064321Notes

Reaction equation

HRID 1064321 reaction equation
[OH-].[Na+].[CH3:3][N:4]1[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([NH:22]C(=O)C)=[CH:18][CH:17]=3)[N:10]=2)=[CH:7][N:6]=[C:5]1[CH3:26]>C(O)(C)C.O>[CH3:3][N:4]1[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)[N:10]=2)=[CH:7][N:6]=[C:5]1[CH3:26]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22273529HCID 22273529, compound

Product 1

HCID 22273502HCID 22273502, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Sodium hydroxide (1.2 g, 3.0 mmole) was added to a solution of 4-(1,2-dimethyl-imidazol-5-yl)-2-(4-acetamidoanilino)pyrimidine (Example 164; 1.25 g, 3.88 mmole) in isopropanol (12 mL) and water (0.5 mL) and the mixture heated under reflux for 90 minutes. The mixture was allowed to cool and was partitioned between saturated aqueous sodium hydrogen carbonate solution and EtOAc. The organic layer was separated and the volatiles evaporated. The residue was purified by column chromatography on silica gel eluting with DCM/7M methanolic ammonia (96:4) to give the title compound (0.75 g, 69%) as a brown solid. NMR: 2.33 (s, 3H), 3.85 (s, 3H), 4.75 (brs, 2H), 6.51 (d, 2H), 6.92 (d, 1H), 7.22 (d, 2H), 7.51 (s, 1H), 8.22 (d, 1H), 8.90 (s, 1H); m/z 281.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 90 minutes
  3. temperatureto cool
  4. customwas partitioned between saturated aqueous sodium hydrogen carbonate solution and EtOAc
  5. customThe organic layer was separated
  6. customthe volatiles evaporated
  7. customThe residue was purified by column chromatography on silica gel eluting with DCM/7M methanolic ammonia (96:4)

Sources & evidence

ORD record
ord-e03df32f0e2f440ab52e4338fdca5022
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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