Picolyl chloride hydrochloride → HCID 9901240, compound

HRID 1355955Notes

Reaction equation

HRID 1355955 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[S:15])[C:5]([C:13]#[N:14])=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1.CC[O-].[Na+].Cl.Cl[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1>C(O)C>[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][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[N:3]=1

Participants

5

Reactant 3

HCID 23392Picolyl chloride hydrochlorideHCID 2723922Sodium ethoxideHCID 178509388HCID 178509388, compound

Product 1

HCID 9901240HCID 9901240, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 200 mg (0.92 mmol) 2-amino-4-furan-2-yl-6-thioxo-1,6-dihydro-pyrimidine-5-carbonitrile in 10 ml ethanol were added 0.69 (1.84 mmol) sodium ethylate solution (2.67M in ethanol) and 117 mg (0.92 mmol) 2-(chloromethyl)pyridine hydrochloride and stirring continued for 16 hours at room temperature. The reaction mixture was then concentrated in vacuo and the residue partitioned between dichloromethane and water. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was triturated in ether to afford 205 mg (72%) 2-amino-4-furan-2-yl-6-(pyridin-2-ylmethylsulfanyl)-pyrimidine-5-carbonitrile as a white crystalline solid. ES-MS m/e (%): 310 (M+H+, 100).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue partitioned between dichloromethane and water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated in ether

Sources & evidence

ORD record
ord-0d5c33ebf1f049e6b7b0fa5a49006bbd
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

Loading…