Thionyl Chloride → 2-((3-Fluorophenyl)amino)-4-(propylamino)pyrimidine-5-carbonyl chloride

HRID 2284709Notes

Reaction equation

HRID 2284709 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][CH3:18])[C:12]([C:19]([OH:21])=O)=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.S(Cl)([Cl:24])=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][CH3:18])[C:12]([C:19]([Cl:24])=[O:21])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 900521172-((3-Fluorophenyl)amino)-4-(propylamino)pyrimidine-5-carboxylic acid

Product 1

HCID 900522012-((3-Fluorophenyl)amino)-4-(propylamino)pyrimidine-5-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 2-((3-fluorophenyl)amino)-4-(propylamino)pyrimidine-5-carboxylic acid (E22, 19 mg), thionyl chloride (2 mL) was added at room temperature, and the mixture was stirred for 2 hours under reflux by heating. The reaction mixture was cooled to room temperature, and then toluene was added to the mixture. The solvent was evaporated under reduced pressure to obtain 2-((3-fluorophenyl)amino)-4-(propylamino)pyrimidine-5-carbonyl chloride (E23) as white solid.

Workup

  1. temperatureunder reflux
  2. temperatureby heating
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-220c3a60957641e58e46f3bd9b3837b4
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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