Sodium Hydroxide → Aditeren

HRID 414517

Reaction equation

HRID 414517 reaction equation
C(OC(=O)[NH:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([CH2:14][C:15]2[C:16]([NH2:22])=[N:17][C:18]([NH2:21])=[N:19][CH:20]=2)=[CH:8][C:7]=1[O:23][CH3:24])C.[OH-].[Na+]>C(O)C>[NH2:21][C:18]1[N:17]=[C:16]([NH2:22])[C:15]([CH2:14][C:9]2[CH:8]=[C:7]([O:23][CH3:24])[C:6]([NH2:5])=[C:11]([O:12][CH3:13])[CH:10]=2)=[CH:20][N:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 540837614-[(2,4-Diamino-5-pyrimidinyl)-methyl]-2,6-dimethoxy-carbanilic acid ethyl ester

Product 1

HCID 176875Aditeren

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 1.04 g. of 4-[(2,4-diamino-5-pyrimidinyl)-methyl]-2,6-dimethoxy-carbanilic acid ethyl ester in a mixture of 50 ml. of 4N sodium hydroxide and 50 ml. of ethanol was boiled under reflux for 18 hours, whereby a solution gradually resulted. The alcohol was removed under vacuum. After standing at room temperature for 1 hour, the crystallized 2,4-diamino-5-(4-amino-3,5-dimethoxy-benzyl)-pyrimidine was removed by filtration with suction, washed with water, recrystallized from methanol and had a melting point of 215°-216° C.

Workup

  1. additionA suspension of 1.04 g
  2. temperatureunder reflux for 18 hours
  3. customwhereby a solution gradually resulted
  4. customThe alcohol was removed under vacuum
  5. customthe crystallized 2,4-diamino-5-(4-amino-3,5-dimethoxy-benzyl)-pyrimidine was removed by filtration with suction
  6. washwashed with water
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-90c5637951a24fd28c9d14d157a929dc
Source dataset
uspto-grants-1988_12
Patent number
US04792557

Linked notes

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