Sodium Hydroxide → HCID 22674310, compound

HRID 1005982Notes

Reaction equation

HRID 1005982 reaction equation
C(O[C:6](=O)[N:7](C)[C:8]1[C:9]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])=[N:10][C:11]([S:14][CH3:15])=[N:12][CH:13]=1)(C)(C)C.[OH-].[Na+]>C(Cl)Cl>[CH3:6][NH:7][C:8]1[C:9]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])=[N:10][C:11]([S:14][CH3:15])=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69924352HCID 69924352, compound

Product 1

HCID 22674310HCID 22674310, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.60 g (4.43 mmol) methyl-(2-methylsulfanyl-4-o-tolyloxy-pyrimidin-5-yl)-carbamic acid tert.-butyl ester in 20 ml CH2Cl2 2 ml trifluoracetic acid was added and the reaction mixture stirred for 2 hrs. at 40°. The reaction mixture was poured into ice-water and the pH of the solution adjusted to 10 with 1N NaOH solution. The aqueous phase was extracted three times with 80 ml CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and evaporated to give 1.10 g (95%) methyl-(2-methylsulfanyl-4-o-tolyloxy-pyrimidin-5-yl)-amine as a white solid, MS (EI): 261 (M+).

Workup

  1. customat 40°
  2. extractionThe aqueous phase was extracted three times with 80 ml CH2Cl2
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-6ed567f1d24e404594f54246f1522fa7
Source dataset
uspto-grants-2004_09
Patent number
US06787539B2

Reaction notes

Loading…