Sodium Hydroxide → HCID 22674282, compound

HRID 1005990Notes

Reaction equation

HRID 1005990 reaction equation
C(O[C:6](=O)[N:7](C)[C:8]1[C:9]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[N:10][C:11]([CH3:14])=[N:12][CH:13]=1)(C)(C)C.[OH-].[Na+]>C(Cl)Cl>[CH3:6][NH:7][C:8]1[C:9]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[N:10][C:11]([CH3:14])=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69924778HCID 69924778, compound

Product 1

HCID 22674282HCID 22674282, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.90 g (5.77 mmol) methyl-(2-methyl-4-o-tolyloxy-pyrimidin-5-yl)-carbamic acid tert.-butyl ester in 25 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 0.95 g (72%) methyl-(2-methyl-4-o-tolyloxy-pyrimidin-5-yl)-amine as a light yellow solid, MS (EI): 229.2 (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-122371de566a41c3a1858ceabd17c95c
Source dataset
uspto-grants-2004_09
Patent number
US06787539B2

Reaction notes

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