Sodium Hydroxide → Aronixil

HRID 637933Notes

Reaction equation

HRID 637933 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][NH:6][C:7]1[N:12]=[C:11]([Cl:13])[CH:10]=[C:9]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:16]=2[CH3:22])[N:8]=1)C.[OH-].[Na+]>C(O)C.O>[Cl:13][C:11]1[CH:10]=[C:9]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:16]=2[CH3:22])[N:8]=[C:7]([NH:6][CH2:5][C:4]([OH:23])=[O:3])[N:12]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13413749Ethyl 4-chloro-6-(2,3-xylidino)-2-pyrimidinylaminoacetate

Product 1

HCID 170355Aronixil

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To the suspension of N-[4-chloro-6-(2,3-xylidino)-2-pyrimidinyl]-aminoacetic acid ethyl ester (2.23 g; examples 3a and 5) in ethanol (27 ml) at 60° C., 1N NaOH (13.5 ml) is added, and the mixture is heated for 5'; then diluted with water, evporated under vacuum and extracted with diethyl ether (2×20 ml). After acidification with glacial acetic acid, the precipitate is filtered and washed with water to neutrality. The solid is then dried under vacuum with CaCT2, and 1.9 g of the desired acid are obtained (I, 1). With the same method the following compounds have been prepared:

Workup

  1. temperaturethe mixture is heated for 5'
  2. extractionextracted with diethyl ether (2×20 ml)
  3. filtrationAfter acidification with glacial acetic acid, the precipitate is filtered
  4. washwashed with water to neutrality
  5. dry with materialThe solid is then dried under vacuum with CaCT2, and 1.9 g of the desired acid
  6. customare obtained (I, 1)
  7. customWith the same method the following compounds have been prepared

Sources & evidence

ORD record
ord-5ea31f27e1b74516a253af04e44fe88b
Source dataset
uspto-grants-1985_12
Patent number
US04559345

Reaction notes

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