Water → HCID 18507455, compound

HRID 1356164Notes

Reaction equation

HRID 1356164 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][C:10]([CH2:13]Br)=[CH:11][CH:12]=2)[C:5]([C:15]#[N:16])=[C:4]([S:17][CH3:18])[N:3]=1.[OH2:19]>CC(C)=O.[N+]([O-])([O-])=O.[Ag+]>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][C:10]([CH2:13][OH:19])=[CH:11][CH:12]=2)[C:5]([C:15]#[N:16])=[C:4]([S:17][CH3:18])[N:3]=1

Participants

5

Reactant 2

HCID 962WaterHCID 18507253HCID 18507253, compound

Product 1

HCID 18507455HCID 18507455, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolvent

Procedure

To a stirred suspension of 100 mg (0.31 mmol) 2-amino-4-(5-bromomethyl-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile in 5 ml water and 5 ml acetone was added 104 mg (0.61 mmol) silver nitrate and stirring continued for 16 h at room temperature in the dark. The reaction mixture was then concentrated in vacuo and the residue partitioned between ethyl acetate and water. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Chromatography (1/1 ethyl acetate/hexane then acetone) afforded 28 mg (35%) 2-amino-4-(5-hydroxymethyl-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile e as an orange crystalline solid. EI-MS m/e (%): 262 (M+, 100), 261 ([M—H]+, 90).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate and water
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5dc6a7ee23ea43fbb0b18e9828050124
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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