Ethyl 2,4-dichloropyrimidine-5-carboxylate → HCID 58169488, compound

HRID 1484858Notes

Reaction equation

HRID 1484858 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=1.[CH:14]1([C:17]2[NH:21][N:20]=[C:19]([NH2:22])[CH:18]=2)[CH2:16][CH2:15]1>CCO>[Cl:1][C:2]1[N:7]=[C:6]([NH:22][C:19]2[CH:18]=[C:17]([CH:14]3[CH2:16][CH2:15]3)[NH:21][N:20]=2)[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 104020Ethyl 2,4-dichloropyrimidine-5-carboxylateHCID 27580143-cyclopropyl-1H-pyrazol-5-amine

Product 1

HCID 58169488HCID 58169488, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of ethyl 2,4-dichloropyrimidine-5-carboxylate (3.6 g, 16.3 mmol, 1.0 equiv.) and 5-cyclopropyl-1H-pyrazol-3-amine (3.0 g, 24.45 mmol, 1.5 equiv.) in EtOH (6 mL) was stirred at 20° C. under a nitrogen atmosphere for 10 min. The reaction mixture was filtered and the solid was washed by EtOH (10 mL) and MeOH (3 mL) to afford ethyl 2-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidine-5-carboxylate (3.5 g, 70%) as a white solid. LC-MS (m/z)=308.1 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was washed by EtOH (10 mL) and MeOH (3 mL)

Sources & evidence

ORD record
ord-531c80f6857d48a39b7b5ea237fe4e66
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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