Sodium Hydroxide → HCID 136401064, compound

HRID 1355815Notes

Reaction equation

HRID 1355815 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:13]#[N:14])=[C:4](SC)[N:3]=1.[OH-:17].[Na+]>O1CCOCC1>[NH2:1][C:2]1[NH:3][C:4](=[O:17])[C:5]([C:13]#[N:14])=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12451273HCID 12451273, compound

Product 1

HCID 136401064HCID 136401064, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 4.2 g (18.1 mmol) 2-amino-4-(2-furyl)-6-(methylthio)-pyrimidine-5-carbonitrile in 50 ml dioxane was added 50 ml (100 mmol) 2M sodium hydroxide solution and the mixture heated at reflux for 16 h. The reaction mixture was then concentrated in vacuo and the residue resuspended in 300 ml ethyl acetate and the mixture stirred for 30 minutes. The resulting crystals were collected by filtration and dried in vacuo. They were then dissolved in 150 ml water and the mixture neutralised with 1M hydrochloric acid. The resulting crystals were collected by filtration and washed with water to afford 3.3 g (90%) 2-amino-4-furan-2-yl-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile as an off-white crystalline solid. ES-MS m/e (%): 201 ([M—H]−, 100).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 16 h
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. filtrationThe resulting crystals were collected by filtration
  5. customdried in vacuo
  6. dissolutionThey were then dissolved in 150 ml water
  7. filtrationThe resulting crystals were collected by filtration
  8. washwashed with water

Sources & evidence

ORD record
ord-75db5f3bf27a42728b70ef797e1216e4
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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