Diethyl methylmalonate → HCID 178431790, compound

HRID 624081Notes

Reaction equation

HRID 624081 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[CH3:5][CH:6]([C:12](OCC)=[O:13])[C:7](OCC)=[O:8].C[O-].[Na+]>CCO>[SH:3][C:2]1[N:4]=[C:7]([OH:8])[C:6]([CH3:5])=[C:12]([OH:13])[N:1]=1

Participants

5

Reactant 3

HCID 11857Diethyl methylmalonateHCID 2723790ThioureaHCID 10942334Sodium Methoxide

Product 1

HCID 178431790HCID 178431790, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cooled solution of thiourea (1 g, 13.14 mmol) and diethyl methylmalonate (3.4 mL, 19.71 mmol) in EtOH (15 mL), NaOMe (2.68 g, 39.41 mmol) was added portionwise. After stirring at 0° C. for 30 min, the reaction was allowed to reach rt and was stirred for another 3 h at rt. The mixture was quenched with diluted acetic acid and the solid was filtered off to yield 2-mercapto-5-methylpyrimidine-4,6-diol as a white solid which was used in the next step without further purification. LC-MS conditions A: tR=0.21 min, [M+H]+=159.11.

Workup

  1. additionwas added portionwise
  2. customto reach rt
  3. stirringwas stirred for another 3 h at rt
  4. customThe mixture was quenched with diluted acetic acid
  5. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-e86369ec2a3a4d759ea05ecc3bb55a87
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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