Diethyl (ethoxymethylene)malonate → Ethyl 2-(4-fluoro-1H-pyrazol-1-yl)-4-hydroxypyrimidine-5-carboxylate

HRID 1525301Notes

Reaction equation

HRID 1525301 reaction equation
Cl.[F:2][C:3]1[CH:4]=[N:5][N:6]([C:8]([NH2:10])=[NH:9])[CH:7]=1.C[O-].[Na+].C([O:16][CH:17]=[C:18]([C:24](OCC)=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])C>CCO>[F:2][C:3]1[CH:4]=[N:5][N:6]([C:8]2[N:10]=[C:17]([OH:16])[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][N:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 10942334Sodium MethoxideHCID 717433874-Fluoro-1H-pyrazole-1-carboximidamide hydrochloride

Product 1

HCID 178469812Ethyl 2-(4-fluoro-1H-pyrazol-1-yl)-4-hydroxypyrimidine-5-carboxylateYield 62.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 28-e (2 g, 12 mmol) in EtOH was added sodium methoxide (1 g, 18 mmol) and diethyl ethoxymethylenemalonate (2.64 g, 12 mmol). The reaction was cooled to room temperature, filtered and washed with EtOH and Et2O to afford the title product, 28-f, (1.9 g, 61%).

Workup

  1. filtrationfiltered
  2. washwashed with EtOH and Et2O

Sources & evidence

ORD record
ord-93c23eec8f9a4e058021c389330afec4
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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