Water → 2-Amino-4-(5-cyano-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile

HRID 1356174Notes

Reaction equation

HRID 1356174 reaction equation
[C:1]([C:3](=[C:13]([S:16][CH3:17])SC)[C:4]([C:6]1[O:10][C:9]([C:11]#[N:12])=[CH:8][CH:7]=1)=O)#[N:2].[N+]([O-])(O)=O.[NH2:22][C:23]([NH2:25])=[NH:24].C(N(CC)CC)C.O>CN(C=O)C>[NH2:25][C:23]1[N:24]=[C:4]([C:6]2[O:10][C:9]([C:11]#[N:12])=[CH:8][CH:7]=2)[C:3]([C:1]#[N:2])=[C:13]([S:16][CH3:17])[N:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10481Guanidine NitrateHCID 865837605-(2-Cyano-3,3-bis-methylsulfanyl-acryloyl)-furan-2-carbonitrile

Product 1

HCID 185073822-Amino-4-(5-cyano-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrileYield 41.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the method of Rudorf and Augustin (J. Prakt. Chem. 1978, 320, 576), a solution of 300 mg (1.13 mmol) 5-(2-cyano-3,3-bis-methylsulfanyl-acryloyl)-furan-2-carbonitrile, 166 mg (1,36 mmol) guanidine nitrate and 0.40 ml (2.84 mmol) triethylamine in 5 ml DMF was heated at reflux for 1 h. The reaction mixture was then cooled to room temperature and poured onto 250 ml water, extracted three times with ethyl acetate, and the combined organic phases dried over sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate) afforded 120 mg (41%) 2-amino-4-(5-cyano-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile as a light yellow crystalline solid. ES-MS m/e (%): 256 ([M—H]−, 100).

Workup

  1. temperatureat reflux for 1 h
  2. extractionextracted three times with ethyl acetate
  3. dry with materialthe combined organic phases dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-23acd4c25b924a8ab360e86d0eb281f4
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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