2-amino-4-phenyl-1H-pyrrole-3-carbonitrile → 5-Phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 1004604Notes

Reaction equation

HRID 1004604 reaction equation
[C:1]([C:3]1[C:7]([C:8]2[CH:13]=[CH:12][C:11](OC)=[CH:10][CH:9]=2)=[CH:6][NH:5][C:4]=1[NH:16][CH:17]=[NH:18])#[N:2].NC1NC=C(C2C=CC=CC=2)C=1C#N>C(OCC)(OCC)OCC>[C:8]1([C:7]2[C:3]3[C:1]([NH2:2])=[N:18][CH:17]=[N:16][C:4]=3[NH:5][CH:6]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 27668732-amino-4-phenyl-1H-pyrrole-3-carbonitrileHCID 178488786HCID 178488786, compound

Product 1

HCID 53577645-Phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Conditions

Temperature
140 °C

Procedure

N-[3-Cyano-4-(4-methoxy-phenyl)-1H-pyrrol-2-yl]-formamidine: 6.0 g of 2-amino-4-phenyl-1H-pyrrole-3-carbonitrile are dissolved in 80 ml of triethyl orthoformate, and the solution is stirred for 1 hour at 140° C. The triethyl orthoformate is removed under a high vacuum and the residue is dissolved in methanol saturated with ammonia. Stirring is carried out for 24 hours at room temperature, followed by filtration. The product is recrystallised from ethanol. M.p.: 238-239° C.

Workup

  1. customThe triethyl orthoformate is removed under a high vacuum
  2. dissolutionthe residue is dissolved in methanol saturated with ammonia
  3. stirringStirring
  4. waitis carried out for 24 hours at room temperature
  5. filtrationfollowed by filtration
  6. customThe product is recrystallised from ethanol

Sources & evidence

ORD record
ord-21eb41dcca5947c69200a28d2ddf9277
Source dataset
uspto-grants-2000_04
Patent number
US06051577

Reaction notes

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