Hydrochloric Acid → 6-Chloro-N-(1H-indol-1-yl)-4-pyrimidinamine

HRID 1646389Notes

Reaction equation

HRID 1646389 reaction equation
C(O)(C)C.Cl[C:6]1[CH:11]=[C:10]([Cl:12])[N:9]=[CH:8][N:7]=1.Cl.[N:14]1([NH2:23])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15]1>O>[Cl:12][C:10]1[N:9]=[CH:8][N:7]=[C:6]([NH:23][N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 709434,6-DichloropyrimidineHCID 6432211-Aminoindole

Product 1

HCID 151582436-Chloro-N-(1H-indol-1-yl)-4-pyrimidinamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To 250 ml isopropanol, was added 4,6-dichloropyrimidine (12 g), 1 ml ethereal -HCl, and 1H-indol-1-amine (15 g). After stirring at 90° C. for seven hours, the mixture was poured into 300 ml iced water, stirred for five minutes, then extracted three times with 200 ml of ethyl acetate. The organic layer was washed with water, then dried (saturated NaCl, anhydrous MgSO4).

Workup

  1. stirringstirred for five minutes
  2. extractionextracted three times with 200 ml of ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried (saturated NaCl, anhydrous MgSO4)

Sources & evidence

ORD record
ord-91aaf4bd026f4472a69dc07252e8f39d
Source dataset
uspto-grants-1993_01
Patent number
US05179204

Reaction notes

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