Benzylamine → N-benzyl-2-chloropyrimidin-4-amine

HRID 2117641Notes

Reaction equation

HRID 2117641 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[CH2:9]([NH:16][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 775312,4-DichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 1712887N-benzyl-2-chloropyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2,4-dichloropyrimidine (0.500 g, 3.36 mmol) in isopropanol (10 mL) was cooled to 0° C., and benzylamine (0.360 g, 0.37 mL, 3.36 mmol) was added. N,N-Diisopropylethylamine (0.434 g, 0.58 mL, 3.4 mmol) was added and the mixture was allowed to warm to room temperature over 15 h. The resulting white suspension was concentrated to afford a white solid. This material was purified via column chromatography on silica gel (gradient elution with 0-50% ethyl acetate-hexane) to afford benzyl-(2-chloropyrimidin-4-yl)amine as a white solid. MS (MH+) 220.1; Calculated 219.68 for C11H10ClN3.

Workup

  1. concentrationThe resulting white suspension was concentrated
  2. customto afford a white solid
  3. customThis material was purified via column chromatography on silica gel (gradient elution with 0-50% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-1c719589f65547ceba9b2ed2370e4bef
Source dataset
uspto-grants-2008_10
Patent number
US07442698B2

Reaction notes

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