Sodium Hydroxide → HCID 20278353, compound

HRID 1248077Notes

Reaction equation

HRID 1248077 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17]([N:20]=[C:21]=[O:22])(=[O:19])=[O:18].[OH-].[Na+]>C(#N)C.O>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([CH3:10])[N:3]=[C:2]([NH:1][C:21]([NH:20][S:17]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=2)(=[O:18])=[O:19])=[O:22])[N:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5872364-Methoxy-6-methylpyrimidin-2-amineHCID 21288567HCID 21288567, compound

Product 1

HCID 20278353HCID 20278353, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 1.4 g of 2-amino-4-methoxy-6-methylpyrimidine in 20 ml of dry acetonitrile at room temperature is added 2.2 g of 2-pyridinesulfonylisocyanate. The mixture is stirred for several hours and filtered. Evaporation of the filtrate yields a solid residue which is stirred in approximately 30 ml of water while adjusting the pH of this mixture to 11 by the addition of 10% NaOH. This solution is filtered, the filtrate pH adjusted to pH 7 by adding 10% hydrochloric acid and the resulting neutral solution again filtered. The desired product is then precipitated from this filtrate by adjusting the pH to 2, collecting in a sintered funnel and drying in a vacuum oven at room temperature.

Workup

  1. filtrationfiltered
  2. customEvaporation of the filtrate
  3. customyields a solid residue which
  4. filtrationThis solution is filtered
  5. additionby adding 10% hydrochloric acid
  6. filtrationthe resulting neutral solution again filtered
  7. customThe desired product is then precipitated from this filtrate
  8. customcollecting in a sintered funnel
  9. customdrying in a vacuum oven at room temperature

Sources & evidence

ORD record
ord-5d4407e1a87e4b07a18f3e7774105163
Source dataset
uspto-grants-1985_06
Patent number
US04522645

Reaction notes

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