Acetic Anhydride → HCID 86231878, compound

HRID 1161657Notes

Reaction equation

HRID 1161657 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][CH:9]=2)[N:5]=[C:4]([NH2:17])[N:3]=1.[C:18](OC(=O)C)(=[O:20])C>O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH3:16])=[CH:12][CH:13]=2)[N:5]=[C:4]([NH:17][CH:18]=[O:20])[N:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 58626071HCID 58626071, compound

Product 1

HCID 86231878HCID 86231878, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound 4-chloro-6-(4-ethoxy-phenyl)-pyrimidin-2-ylamine (0.4 g, 1.6 mmol) and acetic anhydride (0.98 g, 9.61 mmol) was stirred at 80° C. for 12 hours. After completion the reaction mixture was poured into cold water (50 mL) and stirred for 10 to 15 minutes at temperature in the range of 20-40° C. The mixture was extracted with dichloromethane, washed with water, dried over anhydrous sodium sulphate, and concentrated. The residue thus obtained was purified by column chromatography using ethyl acetate-petroleum ether to afford the desired compound. Yield: 71%.

Workup

  1. stirringstirred for 10 to 15 minutes at temperature in the range of 20-40° C
  2. extractionThe mixture was extracted with dichloromethane
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customThe residue thus obtained
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-15805dce9c814573909562e043f6b87a
Source dataset
uspto-grants-2010_10
Patent number
US07820654B2

Reaction notes

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