Hydrochloric Acid → 2-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 2189288Notes

Reaction equation

HRID 2189288 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:5](/[CH:14]=[CH:15]\OCC)=[CH:4][N:3]=1.Cl>CCO>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:14]=[CH:15][N:8]([CH:9]([CH2:10][CH3:11])[CH2:12][CH3:13])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58015730[2-Chloro-5-((Z)-2-ethoxy-vinyl)-pyrimidin-4-yl]-(1-ethylpropyl)-amine

Product 1

HCID 580159322-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of [2-chloro-5-((Z)-2-ethoxy-vinyl)-pyrimidin-4-yl]-(1-ethylpropyl)-amine (1.1 g, 4.07 mmol) in EtOH (8 mL) is added concentrated HCl (0.1 mL) at ambient temperature. The reaction mixture is sealed in a microwave reactor and heated at 100° C. for 10 min. After cooling to room temperature, the mixture is concentrated in vacuo to provide 2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine. The crude product is used as it is. The crude product can be purified by flash chromatography (SiO2, EtOAc/Hexane 1:5).

Workup

  1. customThe reaction mixture is sealed in a microwave reactor
  2. temperatureAfter cooling to room temperature
  3. concentrationthe mixture is concentrated in vacuo

Sources & evidence

ORD record
ord-e9463cee112e40268844c1cde8aeb677
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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