Hydrochloric Acid → 4-Chloro-6-(indolin-1-yl)pyrimidin-5-amine

HRID 1946589Notes

Reaction equation

HRID 1946589 reaction equation
[NH2:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[N:6][C:7]=1[Cl:8].[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11]1.Cl>C(O)C.O>[Cl:8][C:7]1[C:2]([NH2:1])=[C:3]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)[N:4]=[CH:5][N:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10328IndolineHCID 794345-Amino-4,6-dichloropyrimidine

Product 1

HCID 234774564-Chloro-6-(indolin-1-yl)pyrimidin-5-amineYield 34.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirring slurry of 5-amino-4,6-dichloropyrimidine (3 g, 18.29 mmol) and indoline (2.057 mL, 18.29 mmol) in ethanol (7 mL) and water (43 mL) was added concentrated aqueous HCl (600 μL) and the mixture was refluxed for 3 h and left to stir at room temperature overnight. The reaction mixture was extracted with ethyl acetate, washed with water, brine, dried over MgSO4 and solvent evaporated. The resulting residue was triturated in 25% ethyl acetate in hexanes for 1 h then filtered to afford title compound 105 (1.55 g, 34%) as a tan solid. LRMS (ESI): (calc) 246.07 (found) 247.2 (MH)+.

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. waitleft
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over MgSO4 and solvent
  6. customevaporated
  7. customThe resulting residue was triturated in 25% ethyl acetate in hexanes for 1 h
  8. filtrationthen filtered

Sources & evidence

ORD record
ord-08f40fd5706e41b38553fabd87bac416
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

Loading…