Ethanol → Ethyl 4-hydrazinopyrimidine-5-carboxylate

HRID 1584851Notes

Reaction equation

HRID 1584851 reaction equation
ClC1N=CC(C(Cl)=O)=CN=1.C(O)C.Cl[C:15]1[N:20]=[CH:19][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][N:16]=1.[NH2:26][NH2:27]>>[NH:26]([C:17]1[C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][N:20]=[CH:15][N:16]=1)[NH2:27]

Participants

5

Reactant 4

HCID 702EthanolHCID 9321HydrazineHCID 104878152-Chloro-pyrimidine-5-carboxylic acid ethyl ester2×HCID 106311292-Chloropyrimidine-5-carbonyl chloride

Product 1

HCID 21220648Ethyl 4-hydrazinopyrimidine-5-carboxylateYield 44%

Procedure

The title compound was prepared by (a) treating 2-chloropyrimidine-5-carbonylchloride (Example 13, 110 mg, 0.62 mmol) with ethanol (200 mg, 4.4 mmol in 1 mL of ethyl acetate) to provide 60% of ethyl 2-chloropyrimidine-5-carboxylate, (b) reaction of ethyl 2-chloropyrimidine-5-carboxylate (70 mg, 0.37 mmol) with hydrazine (100 mg, 3 mmol) to afford 44% of ethyl 4-hydrazinopyrimidine-5-carboxylate as in Example 19, (c) reaction of ethyl 4-hydrazinopyrimidine-5-carboxylate (0.36 g, 2.0 mmol) with citraconic anhydride (0.34 g, 3.0 mmol) in analogy to Example 21 to afford 10% (0.05 g) of the title compound; m.p. 95-98° C.

Workup

  1. customto provide

Sources & evidence

ORD record
ord-b1337df3f0094a7baeece8cfaeee93a2
Source dataset
uspto-grants-1999_08
Patent number
US05935966

Reaction notes

Loading…