Cyclopentylamine → N4-cyclopentylpyrimidine-2,4-diamine

HRID 876015Notes

Reaction equation

HRID 876015 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH:9]1([NH2:14])[CH2:13][CH2:12][CH2:11][CH2:10]1.C(N(CC)CC)C>CCO>[CH:9]1([NH:14][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 2233322-Amino-4-chloropyrimidine

Product 1

HCID 58299890N4-cyclopentylpyrimidine-2,4-diamineYield 84.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 2-amino-4-chloropyrimidine (22.8 g, 176 mmol), cyclopentylamine (20.9 mL, 211 mmol) and triethylamine (29.4 mL, 211 mmol) in EtOH (200 mL) was heated at reflux (105° C., oil bath) for 48 h. Upon workup, the volatile was removed in vacuo. The residue was poured into ice and saturated Na2CO3 aqueous solution and extracted with ethyl acetate (3×). The combined organics were washed with saturated Na2CO3 aqueous solution (1×), dried over Na2SO4, and concentrated in vacuo to give N4-cyclopentylpyrimidine-2,4-diamine (315) (26.5 g) as a light yellow solid of 92% purity. This batch of material was taken onto the next step without further purification. LCMS-ESI (POS), M/Z, M+1: Found 179.1, Calculated 179.1.

Workup

  1. temperaturewas heated
  2. customUpon workup, the volatile was removed in vacuo
  3. additionThe residue was poured into ice and saturated Na2CO3 aqueous solution
  4. extractionextracted with ethyl acetate (3×)
  5. washThe combined organics were washed with saturated Na2CO3 aqueous solution (1×)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a1f2d085b74d496dac8b40310e9337df
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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