Carbon Dioxide → N-(2-dimethylaminoethyl)-2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)propionamide

HRID 51498Notes

Reaction equation

HRID 51498 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:24]([CH3:30])[C:25](OCC)=[O:26])[C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:31][N:32]([CH3:36])[CH2:33][CH2:34][NH2:35].C(=O)=O>CO>[CH3:31][N:32]([CH3:36])[CH2:33][CH2:34][NH:35][C:25](=[O:26])[CH:24]([N:8]1[C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=2[C:10]([C:11]2[CH:12]=[CH:13][C:14]([O:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:15][CH:16]=2)=[CH:9]1)[CH3:30]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 66053N,N-DimethylethylenediamineHCID 22736339ethyl 2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]propionate

Product 1

HCID 22736284N-(2-dimethylaminoethyl)-2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)propionamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]propionate (425 mg), N,N-dimethylethylenediamine (2 ml) and methanol (20 ml) was boiled under reflux for 18 hours with the exclusion of carbon dioxide. The mixture was cooled and filtered, the filtrate was diluted with water (50 ml) and stirred with ether. The mixture was left standing for 18 hours and the solid which precipitated was collected by filtration, washed with water and then ether and dried to give N-(2-dimethylaminoethyl)-2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)propionamide, m.p. 163-164° C.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. additionthe filtrate was diluted with water (50 ml)
  4. waitThe mixture was left
  5. customthe solid which precipitated
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. dry with materialether and dried

Sources & evidence

ORD record
ord-491ecddd74694791a56ba0b52cd34afe
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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