Sodium Hydroxide → Methyl [6-methyl-2-[(2-thienylsulfonyl)aminocarbonylamino]pyrimidin-4-yloxy]acetate

HRID 2058106Notes

Reaction equation

HRID 2058106 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[C:4]([CH3:14])[N:3]=1.[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[S:20]([N:23]=[C:24]=[O:25])(=[O:22])=[O:21].[OH-].[Na+]>C(Cl)Cl>[CH3:14][C:4]1[N:3]=[C:2]([NH:1][C:24]([NH:23][S:20]([C:16]2[S:15][CH:19]=[CH:18][CH:17]=2)(=[O:21])=[O:22])=[O:25])[N:7]=[C:6]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 12875192Thiophene-2-sulfonyl isocyanateHCID 13469547Methyl (2-amino-6-methylpyrimidin-4-yloxy)acetate

Product 1

HCID 13469548Methyl [6-methyl-2-[(2-thienylsulfonyl)aminocarbonylamino]pyrimidin-4-yloxy]acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dry stirred solution of 18 parts of methyl (2-amino-6-methylpyrimidin-4-yloxy)acetate in 300 parts of methylene chloride at ambient temperature was added 20 parts of 2-thiophenesulfonylisocyanate. The solution was allowed to stand for 3 hours and was then poured onto ice. The pH of the aqueous layer was adjusted to 11 with sodium hydroxide solution and the methylene chloride layer was separated therefrom. The aqueous layer was neutralized with aqueous hydrochloric acid and then extracted with methylene chloride. The extract was dried and stripped of solvent to yield 8 parts of methyl [6-methyl-2-[(2-thienylsulfonyl)aminocarbonylamino]pyrimidin-4-yloxy]acetate, m.p. 114°-120°.

Workup

  1. additionwas then poured onto ice
  2. customthe methylene chloride layer was separated
  3. extractionextracted with methylene chloride
  4. customThe extract was dried

Sources & evidence

ORD record
ord-c4643307161a41b7af31aec0d5bdcde2
Source dataset
uspto-grants-1980_07
Patent number
US04214890

Reaction notes

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