Sodium Carbonate → 6-Chloro-N-(3-methyl-1H-indol-1-yl)-4-pyrimidinamine

HRID 703463Notes

Reaction equation

HRID 703463 reaction equation
CN1CCCC1=O.[CH3:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([NH2:18])[CH:10]=1.[Cl:19][C:20]1[CH:25]=[C:24](Cl)[N:23]=[CH:22][N:21]=1.C([O-])([O-])=O.[Na+].[Na+]>O>[Cl:19][C:20]1[N:21]=[CH:22][N:23]=[C:24]([NH:18][N:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]([CH3:8])=[CH:10]2)[CH:25]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 709434,6-DichloropyrimidineHCID 124272923-Methyl-1H-indol-1-amine

Product 1

HCID 151582466-Chloro-N-(3-methyl-1H-indol-1-yl)-4-pyrimidinamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To 125 ml of 1-methyl-2-pyrrolidinone was added 3-methyl-1H-indol-1-amine (10.0 g), and this mixture was heated to 120° C. Then 4,6-dichloropyrimidine (10.43 g), was added to the hot solution and this mixture was stirred for four hours. The reaction was cooled, poured into water, basified with Na2CO3 (aq) extracted with ethyl acetate and the organic layer washed with water and dried (sat. NaCl, anhy. MgSO4).

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate
  3. washthe organic layer washed with water
  4. dry with materialdried (sat. NaCl

Sources & evidence

ORD record
ord-195fcca5cded465a953955017ceff35f
Source dataset
uspto-grants-1991_01
Patent number
US04983608

Reaction notes

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