Potassium Carbonate → Ethyl 4-chloro-2-(pyridin-3-yl)pyrimidine-5-carboxylate

HRID 2359646Notes

Reaction equation

HRID 2359646 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](O)=[N:8][C:9]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[N:10][CH:11]=1)=[O:5])[CH3:2].O=S(Cl)[Cl:21].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([Cl:21])=[N:8][C:9]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 178469745HCID 178469745, compound

Product 1

HCID 24903914Ethyl 4-chloro-2-(pyridin-3-yl)pyrimidine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of Compound 14c (5.05 g; 20.59 mmol) in DMF (70 mL) was added SOCl2 (3 mL; 41.23 mmol) dropwise at room temperature. The reaction was stirred at room temperature for 30 min, then poured into an ice water slurry of K2CO3 (3.41 g). The resultant solid (Compound 14d) was collected by filtration and dried. 1H NMR (300 MHz, CDCl3): δ 9.70 (s, 1H), 9.20 (s, 1H), 7.70-8.85 (m, 2H), 7.50 (dd, 1H), 4.50 (q, 2H), 1.45 (t, 3H); MS: m/z 264.1 (M+H)+.

Workup

  1. filtrationThe resultant solid (Compound 14d) was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-03e802c62dbe4dc3babd10c9ea6a269a
Source dataset
uspto-grants-2014_04
Patent number
US08685990B2

Reaction notes

Loading…