Sodium Hydroxide → HCID 178524636, compound

HRID 880328Notes

Reaction equation

HRID 880328 reaction equation
C([O:3][C:4](=O)/[C:5](/[O-])=[CH:6]/[C:7]([O:9]CC)=[O:8])C.[Na+].C(O)(=O)C.[CH:19](=[NH:21])[NH2:20].[OH-].[Na+]>O>[OH:3][C:4]1[N:21]=[CH:19][N:20]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 160693Formamidine acetateHCID 16462971HCID 16462971, compound

Product 1

HCID 178524636HCID 178524636, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of sodium (Z)-1,4-diethoxy-1,4-dioxobut-2-en-2-olate (55.0 g, 262 mmol) in H2O (500 mL) was added formimidamide acetate (27.3 g, 262 mmol) and NaOH (10.5 g). After addition, the resulting mixture was stirred at 25° C. for 16 h then concentrated and then acidified by added aqueous HCl (1N) until pH=1. The resulting solid was collected by filtration, washed with H2O and ether to give 6-hydroxypyrimidine-4-carboxylic acid (6.0 g, yield: 16.3%). 1H NMR (400 MHz, DMSO-d6) δ 12.89 (s, 1H), 8.24 (s, 1H), 6.83 (s, 1H).

Workup

  1. additionAfter addition
  2. concentrationthen concentrated
  3. additionby added aqueous HCl (1N) until pH=1
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with H2O and ether

Sources & evidence

ORD record
ord-e32a7e043f494b7a8004c8ae71f74c4c
Source dataset
uspto-grants-2015_03
Patent number
US08993555B2

Reaction notes

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