Ethyl bromoacetate → ethyl 2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]acetate

HRID 51499

Reaction equation

HRID 51499 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][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[H-].[Na+].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>CN(C)C=O>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:15][CH:16]=3)=[CH:9][N:8]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 120422345-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Product 1

HCID 22736383ethyl 2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine (906 mg), sodium hydride (120 mg, of a 60% dispersion in mineral oil) and dry dimethylformamide (30 ml) was stirred at ambient temperature under nitrogen for 30 minutes. Ethyl bromoacetate (0.5 g) in dimethylformamide (10 ml) was added over 5 minutes at 0-5° C. with stirring. The mixture was stirred for 30 minutes at ambient temperature and then allowed to stand for 18 hours. The mixture was evaporated under vacuum and the residue was triturated with water and ether. The solid obtained was collected by filtration, washed with water and then with ether to give ethyl 2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]acetate, m.p. 161-161.3° C.

Workup

  1. stirringThe mixture was stirred for 30 minutes at ambient temperature
  2. customThe mixture was evaporated under vacuum
  3. customthe residue was triturated with water and ether
  4. customThe solid obtained
  5. filtrationwas collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-102f74cf58634a9e9db2e05e54ec7f3a
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Linked notes

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