Sodium Hydroxide → 8-cyclobutyl-3-pentyl-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-one

HRID 2368581Notes

Reaction equation

HRID 2368581 reaction equation
[NH2:1][C:2]1[C:7](=[O:8])[NH:6][C:5](=[S:9])[N:4]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:3]=1[NH:15][C:16]([CH:18]1[CH2:21][CH2:20][CH2:19]1)=O.[OH-].[Na+]>O.CO>[CH:18]1([C:16]2[NH:1][C:2]3[C:7](=[O:8])[NH:6][C:5](=[S:9])[N:4]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:3]=3[N:15]=2)[CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57600174N-(5-amino-6-oxo-3-pentyl-2-thioxo-1,2,3,6-tetrahydropyrimidin-4-yl)cyclobutanecarboxamide

Product 1

HCID 576002418-cyclobutyl-3-pentyl-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-oneYield 74.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

The mixture of N-(5-amino-6-oxo-3-pentyl-2-thioxo-1,2,3,6-tetrahydropyrimidin-4-yl)cyclobutanecarboxamide (720 mg, 2.3 mmol) and 2.5 M of sodium hydroxide in water (25 mL) and methanol (25 mL) was stirred at 70° C. for 1 hour. After cooling to room temperature, The reaction mixture was concentrated to remove methanol and then acidified to pH=5. The precipitate formed was filtered and dried to yield the desired product (500 mg, 73.7%). LCMS calculated for C14H21N4OS (M+H): 293.1. Found: 293.1.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationThe reaction mixture was concentrated
  3. customto remove methanol
  4. customThe precipitate formed
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-5fe559215cdb4c0d8f2b4c698054c34c
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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