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

HRID 718056Notes

Reaction equation

HRID 718056 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-6572c5fb4f124700a50c36c8077f73a5
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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