Ethanol → 5-Cyano-N-(1H-indol-1-yl)-4-pyrimidinamine

HRID 703467Notes

Reaction equation

HRID 703467 reaction equation
C(O)C.[N:4]1([NH2:13])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.Cl[C:15]1[C:20]([C:21]#[N:22])=[CH:19][N:18]=[CH:17][N:16]=1.C(N(CC)CC)C>O>[C:21]([C:20]1[C:15]([NH:13][N:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=[CH:5]2)=[N:16][CH:17]=[N:18][CH:19]=1)#[N:22]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 6432211-AminoindoleHCID 131269094-Chloropyrimidine-5-carbonitrile

Product 1

HCID 151582525-Cyano-N-(1H-indol-1-yl)-4-pyrimidinamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 100 ml absolute ethanol, was added 5.0 g of 1H-indol-1-amine, 5.0 g of 4-chloro-5-cyanopyrimidine and 5 ml of triethylamine. After stirring at ambient temperature for 20 hours, the mixture was poured into 400 ml water, stirred for five minutes, then extracted with ethyl acetate. The organic layer was washed with water, then dried (saturated NaCl, anhydrous MgSO4).

Workup

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

Sources & evidence

ORD record
ord-e13453b879254b4cb17d43532bcf19a5
Source dataset
uspto-grants-1991_01
Patent number
US04983608

Reaction notes

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