Cyclopropanemethanamine → HCID 90417634, compound

HRID 1486816Notes

Reaction equation

HRID 1486816 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][N:3]=1.[CH:13]1([CH2:16][NH2:17])[CH2:15][CH2:14]1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:13]1([CH2:16][NH:17][C:2]2[N:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][N:3]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 75646CyclopropanemethanamineHCID 81531DiisopropylethylamineHCID 104878152-Chloro-pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 90417634HCID 90417634, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-chloropyrimidine-5-carboxylate (500 mg, 2.68 mmol), cyclopropylmethylamine (0.28 mL, 3.22 mmol) and DIPEA (0.58 mL, 3.35 mmol) were dissolved in DMF (4 mL) and the reaction mixture was heated using a microwave reactor at 100° C. for 20 min. The reaction mixture was concentrated in vacuo and the residue was partitioned between DCM (50 mL) and sat aq NaHCO3 (40 mL). The organic fraction was dried (MgSO4) and concentrated in vacuo to give the title compound (566 mg, 95.5%) as a yellow solid. LCMS (ES+): 222.1 [MH]+. HPLC: Rt 5.79 min, 92.9% purity.

Workup

  1. temperaturethe reaction mixture was heated
  2. customat 100° C.
  3. customfor 20 min
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customthe residue was partitioned between DCM (50 mL)
  6. dry with materialThe organic fraction was dried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a0f70cf3444544beb1db8b9801a772e8
Source dataset
uspto-grants-2016_08
Patent number
US09428498B2

Reaction notes

Loading…