Cyclopropanemethanamine → HCID 58495643, compound

HRID 1191104Notes

Reaction equation

HRID 1191104 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.[CH:9]1([CH2:12][NH2:13])[CH2:11][CH2:10]1.C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1>[Cl:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:13][CH2:12][CH:9]2[CH2:11][CH2:10]2)[N:7]=1

Participants

5

Reactant 3

HCID 75646CyclopropanemethanamineHCID 775312,4-DichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 58495643HCID 58495643, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a microwave reaction vessel, slurry 2,4-dichloropyrimidine (1.0 g, 6.7 mmol), cyclopropylmethylamine (550 μL, 6.0 mmol), and diisopropylethylamine (2.35 mL, 13.4 mmol) in toluene (3 mL). Irradiate in microwave (300 watts) at 120° C. for 30 min. Cool to room temperature and concentrate in vacuo. Purify by chromatography on silica gel (40 g) eluting with hexane/EtOAc (4:1 to 3:7 over 30 min; 40 mL/min) to obtain the desired intermediate (157.5 mg, 15%) as a colorless oil.

Workup

  1. customIrradiate in microwave (300 watts) at 120° C. for 30 min
  2. concentrationconcentrate in vacuo
  3. customPurify by chromatography on silica gel (40 g)
  4. washeluting with hexane/EtOAc (4:1 to 3:7 over 30 min; 40 mL/min)

Sources & evidence

ORD record
ord-412bc0e8d44246c09be412d860358999
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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