2,4-Dichloro-5-fluoropyrimidine → HCID 57562949, compound

HRID 1947615Notes

Reaction equation

HRID 1947615 reaction equation
[F:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1.[Cl:12][C:13]1[N:18]=[CH:17][C:16]([F:19])=[C:15](Cl)[N:14]=1>CO.O>[Cl:12][C:13]1[N:18]=[C:17]([NH:9][C:8]2[CH:10]=[CH:11][C:5]([CH2:4][CH2:3][CH2:2][F:1])=[CH:6][CH:7]=2)[C:16]([F:19])=[CH:15][N:14]=1

Participants

5

Reactant 2

HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 57562911HCID 57562911, compound

Product 1

HCID 57562949HCID 57562949, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

4-(3-Fluoropropyl)aniline and 2,6-dichloro-5-fluoropyrimidine (1.5 g) were dissolved in methanol (5 mL) and water (1 mL). The reaction solution was stirred at rt for 3 d. The reaction solution was diluted with water (100 mL) and extracted with ethyl acetate (2×100 mL). The organic layers were evaporated and purified by flash column chromatography (EtOAc/hexanes=1/4, 1/2) to give 2-chloro-5-fluoro-N4-[4-(3-fluoropropyl)phenyl]-4-pyrimidineamine.

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. customThe organic layers were evaporated
  3. custompurified by flash column chromatography (EtOAc/hexanes=1/4, 1/2)

Sources & evidence

ORD record
ord-d29e541edb0c416290935dc3e35ed7c4
Source dataset
uspto-grants-2013_03
Patent number
US08399472B2

Reaction notes

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