Water → HCID 15158251, compound

HRID 1646397Notes

Reaction equation

HRID 1646397 reaction equation
Cl[C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[N:5]=[CH:4][N:3]=1.[N:10]1([NH2:19])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11]1.O>CN1CCCC1=O>[Cl:9][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:19][N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)[C:7]=1[NH2:8]

Participants

5

Reactant 3

HCID 962WaterHCID 794345-Amino-4,6-dichloropyrimidineHCID 6432211-Aminoindole

Product 1

HCID 15158251HCID 15158251, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 8 g of 4,6-dichloro-5-pyrimidinamine, and 7 g of 1H-indol-1-amine, in 100 ml N-methyl-2-pyrrolidone was stirred at 130°-135° for seven hours, then cooled, stirred with water and extracted with ether. The organic extract was washed with water and saturated sodium chloride, dried (anhy. MgSO4), filtered and evaporated to 16 g of a residue. This was purified by flash chromatography (silica, 5% ethyl acetate/DCM) to give 10 g solid. This was combined with product obtained from other condensations and purified by HPLC (silica 5% ethyl acetate/DCM) to give 7 g oil. This oil was crystallized from ether-petroleum ether to give 2.2 g solid, 6-Chloro-N4 -(1H-indol-1-yl)-4,5-pyrimidinediamine, m.p. 175°-176°.

Workup

  1. temperaturecooled
  2. extractionextracted with ether
  3. extractionThe organic extract
  4. washwas washed with water and saturated sodium chloride
  5. dry with materialdried (anhy. MgSO4)
  6. filtrationfiltered
  7. customevaporated to 16 g of a residue
  8. customThis was purified by flash chromatography (silica, 5% ethyl acetate/DCM)

Sources & evidence

ORD record
ord-9ef656e9bfa748559d24ae20681f824e
Source dataset
uspto-grants-1993_01
Patent number
US05179204

Reaction notes

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