Formaldehyde → 4,6-Dimethyl-2-(4-tolylsulfonylmethylamino)pyrimidine

HRID 1788871

Reaction equation

HRID 1788871 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][S:11]([OH:14])(=O)=[O:12].[C:15]1([CH3:25])[CH:20]=[CH:19]C=[C:17](S(O)(=O)=O)[CH:16]=1.[Na].[CH2:27]=O>O>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[N:7]=[C:2]([NH:1][CH2:27][S:11]([C:10]2[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=2)(=[O:14])=[O:12])[N:3]=1

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 6395Methanesulfonic AcidHCID 130212-Amino-4,6-dimethyl pyrimidineHCID 105362m-Toluenesulfonic acidHCID 5360545Sodium

Product 1

HCID 230432214,6-Dimethyl-2-(4-tolylsulfonylmethylamino)pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

12.7 g (0.1 mole) of 2-amino-4,6-dimethylpyrimidine are suspended in 200 ml of water and then 9.7 g (0.1 mole) of methanesulfonic acid are stirred in to form a solution. To the stirred solution are added, in succession, 18.22 g (0.1 mole) of toluene-3-sulfonic acid, sodium salt, and 9.4 g (0.11 mole) of aqueous 35% formaldehyde. The mixture is stirred for 2 hours at room temperature and for another 30 minutes at 90° C. The colourless precipitate is filtered with suction after cooling and dried. Melting point: 191°-194° C. Yield: 25 g (86% of theory).

Workup

  1. customto form a solution
  2. filtrationThe colourless precipitate is filtered with suction
  3. temperatureafter cooling
  4. customdried

Sources & evidence

ORD record
ord-9ea8c5f23c574b2e8a2a3b12fa410e55
Source dataset
uspto-grants-1987_08
Patent number
US04685961

Linked notes

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