Cyclopropanemethanamine → N4-(cyclopropylmethyl)pyrimidine-2,4-diamine

HRID 875976Notes

Reaction equation

HRID 875976 reaction equation
[CH:1]1([CH2:4][NH2:5])[CH2:3][CH2:2]1.Cl[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[N:8]=1>C(O)C>[CH:1]1([CH2:4][NH:5][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[N:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 75646CyclopropanemethanamineHCID 2233322-Amino-4-chloropyrimidine

Product 1

HCID 20277654N4-(cyclopropylmethyl)pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To cyclopropylmethanamine (3.62 g, 50.9 mmol) in ethanol (90 mL) was added solid 4-chloropyrimidin-2-amine (6.00 g, 46.3 mmol). The reaction was stirred at reflux (100° C. oil bath) for 16 h. The reaction was cooled to room temperature and solvent was removed in vacuo. The product 237 obtained in quantitative yield. LCMS-ESI (POS), M/Z, M+1: Found 165.0, Calculated 165.1.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customsolvent was removed in vacuo

Sources & evidence

ORD record
ord-a13311428a024d01a3010116d1191c91
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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