Dimethylformamide → HCID 178503553, compound

HRID 2353639Notes

Reaction equation

HRID 2353639 reaction equation
Cl[CH2:2][C:3]1[N:8]=[C:7]([S:9][CH3:10])[N:6]=[C:5]([OH:11])[CH:4]=1.[Na+].[CH3:13][S:14]([O-:16])=[O:15].CN(C=O)C>C(#N)C>[CH3:10][S:9][C:7]1[N:6]=[C:5]([OH:11])[CH:4]=[C:3]([CH2:2][S:14]([CH3:13])(=[O:16])=[O:15])[N:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2733271Sodium methanesulfinateHCID 178503549HCID 178503549, compound

Product 1

HCID 178503553HCID 178503553, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

6-(Chloromethyl)-2-methylsulfanyl-pyrimidin-4-ol (19.07 g, 100 mmol) was suspended in acetonitrile (400 ml). To this stirring suspension was added methanesulphinic acid sodium salt (12.255 g, 120 mmol) and DMF (100 ml). The reaction was then heated to 100° C. to give a dark suspension and monitored by LCMS. Once complete, the solvents were removed and the resultant product added to 1:1 MeOH:DCM (200 ml) and acidified with acetic acid (10 ml). The resultant precipitate was collected, washed with water (200 ml) and MeOH (100 ml) and dried overnight in vacuo to afford the title compound as a white solid, 16.45 g.

Workup

  1. customto give a dark suspension
  2. customOnce complete, the solvents were removed
  3. additionthe resultant product added to 1:1 MeOH
  4. customThe resultant precipitate was collected
  5. washwashed with water (200 ml) and MeOH (100 ml)
  6. customdried overnight in vacuo

Sources & evidence

ORD record
ord-f7a7b94b7bf14e9884ad6504c755d549
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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