Cyclopentylamine → 5-Bromo-2-chloro-N-cyclopentyl-4-pyrimidinamine

HRID 875935

Reaction equation

HRID 875935 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH:10]1([NH2:15])[CH2:14][CH2:13][CH2:12][CH2:11]1>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([NH:15][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 2906CyclopentylamineHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 442482475-Bromo-2-chloro-N-cyclopentyl-4-pyrimidinamineYield 101.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-bromo-2,4-dichloropyrimidine (45.6 g, 200 mmol) in dioxane (400 mL) was added N-cyclopentylamine (20.4 g, 240 mmol) at room temperature. The mixture thus obtained was stirred at room temperature for 6 h. The reaction mixture was then diluted with ethyl acetate and washed with brine and dried over MgSO4. The solvent was evaporated to give the title compound as a light yellow solid (56 g, 100%) which was used in next step without further purification. 1H NMR (500 MHz, DMSO-d6) δ 8.23 (1H, s), 7.37 (1H, d, J=7.3 Hz), 4.31 (1H, m), 1.92 (2H, m), 1.71 (2H, m), 1.53-1.59 (4H, m) ppm; LCMS-ESI (POS), M/Z, M+1: Found 276.0, Calculated 275.9.

Workup

  1. customThe mixture thus obtained
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-6d1fbca72748437dbf326f2dd21f2e86
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Linked notes

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