Triethylamine → HCID 52937164, compound

HRID 2236163Notes

Reaction equation

HRID 2236163 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[OH:11][CH:12]1[CH2:16][CH2:15][NH:14][CH2:13]1.C(N(CC)CC)C>C1COCC1>[N+:8]([C:5]1[CH:4]=[N:3][C:2]([N:14]2[CH2:15][CH2:16][CH:12]([OH:11])[CH2:13]2)=[N:7][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 825442-Chloro-5-nitropyrimidineHCID 982104-Hydroxypyrrolidine

Product 1

HCID 52937164HCID 52937164, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-5-nitro-pyrimidine (638 mg, 4 mmol) in THF (15 mL) cooled to 0° C. was added 3-hydroxypyrrolidine (392 mg, 4.5 mmol) and triethylamine (1.2 mL). The mixture was stirred at room temperature overnight. Solids were filtered out and the solution was concentrated. The residue was dissolved in ethyl acetate and extracted with water. Organic layer was washed with dilute aqueous citric acid solution. After the evaporation of solvents, the residue was treated with ether and the yellow solid was filtered to give N-(5-nitro-pyrimidin-2-yl)-pyrrolidin-3-ol (570 mg). LCMS calcd for C8H10N4O3 m/e 210.19, obsd 211.0 (ES, M+H). Hydrogenation of the nitro compound, as above, provided N-(5-aminopyrimidin-2-yl)-pyrrolidin-3-ol.

Workup

  1. filtrationSolids were filtered out
  2. concentrationthe solution was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. extractionextracted with water
  5. washOrganic layer was washed with dilute aqueous citric acid solution
  6. customAfter the evaporation of solvents
  7. additionthe residue was treated with ether
  8. filtrationthe yellow solid was filtered

Sources & evidence

ORD record
ord-8be870efc7dd4760bece1dfa85a108a2
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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