Cyclopropanemethanamine → HCID 22308372, compound

HRID 1191102Notes

Reaction equation

HRID 1191102 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[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>C(O)(C)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:13][CH2:12][CH:9]2[CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 75646CyclopropanemethanamineHCID 775312,4-DichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 22308372HCID 22308372, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a microwave reaction vessel, slurry 2,4-dichloropyrimidine (0.5 g, 3.36 mmol), cyclopropylmethylamine (275 μL, 3.18 mmol), and diisopropylethylamine (1.17 mL, 6.72 mmol) in iso-propanol (2 mL). Irradiate in microwave (300 watts) at 130° C. for 15 min. Cool to room temperature and concentrate in vacuo. Purify by chromatography on silica gel (40 g) eluting with hexane/EtOAc (4:1 to 1:3 over 45 min; 40 mL/min) to obtain the desired intermediate (374 mg, 65%) as a colorless oil.

Workup

  1. customIrradiate in microwave (300 watts) at 130° C. for 15 min
  2. concentrationconcentrate in vacuo
  3. customPurify by chromatography on silica gel (40 g)
  4. washeluting with hexane/EtOAc (4:1 to 1:3 over 45 min; 40 mL/min)

Sources & evidence

ORD record
ord-da24ea2e2a70473dbf77249458191a54
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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