Sodium Hydroxide → HCID 9976966, compound

HRID 1198929Notes

Reaction equation

HRID 1198929 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]3[C:14]([CH3:18])=[C:15]([CH3:17])[S:16][C:10]=3[N:9]([CH2:19][C:20]([O:22]CC)=[O:21])[C:8]2=[O:25])=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[C:20]([CH2:19][N:9]1[C:10]2[S:16][C:15]([CH3:17])=[C:14]([CH3:18])[C:11]=2[C:12](=[O:13])[N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:27][CH:26]=2)[C:8]1=[O:25])([OH:22])=[O:21]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10364000HCID 10364000, compound

Product 1

HCID 9976966HCID 9976966, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A 0.7 g quantity of 3-(4-chlorobenzyl)-1-ethoxycarbonylmethyl-5,6-dimethylthieno[2,3-d]pyrimidin-2,4(1H, 3H)-dione (Compound IV-1) prepared in Reference Example 5 was dissolved in 30 ml of methanol. To the solution was added 0.3 g of sodium hydroxide dissolved in 2 ml of water. The mixture was allowed to react at 60° C. for 30 minutes, and then the reaction mixture was concentrated. Diluted hydrochloric acid was added thereto with ice-cooling to acidify the resulting solution. The solution was filtrated and the separated crystals were recrystallized from methanol, giving 0.4 g of 1-carboxymethyl-3-(4-chlorobenzyl)-5,6-dimethylthieno[2,3-d]pyrimidin-2,4(1H, 3H)-dione having m.p. of 173° to 176° C. in a yield of 61%.

Workup

  1. customto react at 60° C. for 30 minutes
  2. concentrationthe reaction mixture was concentrated
  3. additionDiluted hydrochloric acid was added
  4. temperaturewith ice-cooling
  5. filtrationThe solution was filtrated
  6. customthe separated crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-afdf4b71f0a9448c98155560b6f909b9
Source dataset
uspto-grants-1990_02
Patent number
US04898867

Reaction notes

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