Methanol → 4-amino-N-(2-amino-6-methoxy-pyrimidin-4-yl)-benzenesulfonamide

HRID 610813Notes

Reaction equation

HRID 610813 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16](Cl)[N:15]=[C:14]([NH2:19])[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:20][OH:21]>[Na]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([O:21][CH3:20])[N:15]=[C:14]([NH2:19])[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 107329394-amino-N-(2-amino-6-chloro-pyrimidin-4-yl)-benzenesulfonamide

Product 1

HCID 193535384-amino-N-(2-amino-6-methoxy-pyrimidin-4-yl)-benzenesulfonamideYield 94%

Reagents, catalysts & solvents 1

HCID 5360545SodiumSolvent

Conditions

Temperature
150 °C

Procedure

0.27 g (0.0009 mol) of 4-amino-N-(2-amino-6-chloro-pyrimidin-4-yl)-benzenesulfonamide was dissolved in a solution of 0.23 g of sodium in 20 ml of methanol and stirred in an autoclave at 150° C. for 9 hours. The solvent was distilled off, the residue was added to water and the pH value was adjusted to 4-5 with 1N HCl. The precipitate which thereby separated was filtered off under suction, washed with water and dried. The crystals obtained were triturated in 20 ml of methanol, again filtered off and dried in a high vacuum. There was obtained 0.25 g (94%) of 4-amino-N-(2-amino-6-methoxy-pyrimidin-4-yl)-benzenesulfonamide as beige crystals; m.p.: >250° C. (dec.).

Workup

  1. distillationThe solvent was distilled off
  2. additionthe residue was added to water
  3. customThe precipitate which thereby separated
  4. filtrationwas filtered off under suction
  5. washwashed with water
  6. customdried
  7. customThe crystals obtained
  8. customwere triturated in 20 ml of methanol
  9. filtrationagain filtered off
  10. customdried in a high vacuum

Sources & evidence

ORD record
ord-f48bf2bf55c34a58b4d151e08077cabe
Source dataset
uspto-grants-1999_12
Patent number
US05998665

Reaction notes

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