Chlorosuccinimide → HCID 18507205, compound

HRID 1356137Notes

Reaction equation

HRID 1356137 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]([S:15][CH3:16])[N:3]=1.[Cl:17]N1C(=O)CCC1=O>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][C:10]([Cl:17])=[CH:11][CH:12]=2)[C:5]([C:13]#[N:14])=[C:4]([S:15][CH3:16])[N:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 12451273HCID 12451273, compound

Product 1

HCID 18507205HCID 18507205, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2.03 g (8.73 mmol) 2-amino-4-furan-2-yl-6-methylsulfanyl-pyrimidine-5-carbonitrile in 12 ml DMF was added 1.22 g (9.16 mmol) N-chlorosuccinimide and stirring continued at 50° C. for 2 hours. The reaction mixture was then poured into 500 ml ice-water and the resulting precipitate collected by filtration and washed with water and then ether to afford 2.19 g (94%) 2-amino-4-(5-chloro-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile as a light brown crystalline solid. EI-MS m/e (%): 268 (M{37Cl}+, 22), 267 ([M{37Cl}-H]+, 42), 266 (M{35Cl}+, 64), 265 ([M{35Cl}-H]+, 100), 231 ([M—Cl]+, 37).

Workup

  1. filtrationthe resulting precipitate collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-feb83ff4204d49b19f0b9dd270c51769
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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