Ammonium Hydroxide → Pyrimidine-5-carboxamide

HRID 578147Notes

Reaction equation

HRID 578147 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([O:9]CC)=O)[CH:4]=[N:3][CH:2]=1.[OH-].[NH4+:13]>CO>[N:1]1[CH:6]=[C:5]([C:7]([NH2:13])=[O:9])[CH:4]=[N:3][CH:2]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 4223810Ethyl 5-pyrimidinecarboxylate

Product 1

HCID 351819Pyrimidine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl pyrimidine-5-carboxylate (6.10 g, 40.0 mmol) in methanol (40 mL) was stirred with ammonium hydroxide (4.30 mL, 110 mmol) in a sealed tube at 50° C. for 10 hours. The reaction mixture was then concentrated and the residue was stirred in ethanol/ethyl acetate (v/v 1/4, 50 mL) at ambient temperature for 2 hours. The white precipitate was collected by filtration and dried to give the titled compound. 1H NMR (300 MHz, DMSO-d6) δ 7.85 [s (broad), 1H], 8.33 [s (broad), 1H], 9.18 (s, 2H), 9.32 (s, 1H) ppm; MS (DCI/NH3) m/z 124 (M+H)+, 141 (M+NH4)+.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. filtrationThe white precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-c3ed7c6657a44cfebee39960fc1f903a
Source dataset
uspto-grants-2015_05
Patent number
US09040568B2

Reaction notes

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