Lithium hydroxide, monohydrate → HCID 18425486, compound

HRID 1280566Notes

Reaction equation

HRID 1280566 reaction equation
[CH2:1]([S:8][C:9]1[N:14]=[C:13]2[N:15]([CH2:27][C:28]([O:30]CC)=[O:29])[C:16](=[O:26])[N:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[CH2:18][C:12]2=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>CO.O.C(OCC)(=O)C.O>[CH2:1]([S:8][C:9]1[N:14]=[C:13]2[N:15]([CH2:27][C:28]([OH:30])=[O:29])[C:16](=[O:26])[N:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[CH2:18][C:12]2=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 12991339HCID 12991339, compound

Product 1

HCID 18425486HCID 18425486, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 22728543Water ethylacetateSolvent

Procedure

A mixture of 7-benzylthio-3-(2-chlorophenyl)-1-(ethoxycarbonylmethyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (1.435 g, 3.36 mmol) and lithium hydroxide monohydrate (481 mg, 11.5 mmol) in methanol (10 mL) and water (30 mL) were refluxed for 48 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate/water. The aqueous layer was adjusted to pH 4 and extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated in vacuo to give 1.2 g of 7-benzylthio-3-(2-chlorophenyl)-1-(hydroxycarbonylmethyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one.

Workup

  1. temperaturewere refluxed for 48 hours
  2. extractionextracted with ethyl acetate
  3. customThe combined organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b162ff67349a4cc1918721e83408176e
Source dataset
uspto-grants-2002_09
Patent number
US06451804B1

Reaction notes

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