Triethylamine → 4-Chloro-2-cyclopropyl-5-nitropyrimidine

HRID 2175200Notes

Reaction equation

HRID 2175200 reaction equation
[CH:1]1([C:4]2[NH:9][C:8](=O)[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][N:5]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.P(Cl)(Cl)([Cl:23])=O>ClCCl>[Cl:23][C:8]1[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][N:5]=[C:4]([CH:1]2[CH2:3][CH2:2]2)[N:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 584974342-cyclopropyl-5-nitro-3H-pyrimidin-4-one

Product 1

HCID 567734194-Chloro-2-cyclopropyl-5-nitropyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of the 2-cyclopropyl-5-nitro-3H-pyrimidin-4-one (900 mg, 4.9 mmol) in dichloromethane (15 ml) was added triethylamine (505 mg, 5 mmol). To the clear solution obtained, phosphorous oxychloride (1.5 g, 10 mmol) was slowly added and the reaction mixture kept at room temperature for 2 hours. TLC showed a single spot. The reaction mixture was diluted with dichloromethane, washed with water and dried over MgSO4, filtered and evaporated to dryness to give brown oil. This material was used as such for the next step.

Workup

  1. customTo the clear solution obtained
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto give brown oil

Sources & evidence

ORD record
ord-834e20c56f5f441aa57c6800731ed1ed
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

Loading…