Carbonic acid-guanidine (1:1) → 4-[(2,4-Diamino-5-pyrimidinyl)-methyl]-2,6-dimethoxy-carbanilic acid ethyl ester

HRID 462523Notes

Reaction equation

HRID 462523 reaction equation
[Na].C(=O)(O)O.[NH2:6][C:7]([NH2:9])=[NH:8].[CH2:10]([O:12][C:13](=[O:37])[NH:14][C:15]1[C:20]([O:21][CH3:22])=[CH:19][C:18]([CH2:23][C:24]([C:33]#N)=[CH:25][NH:26]C2C=CC=CC=2)=[CH:17][C:16]=1[O:35][CH3:36])[CH3:11]>C(O)C>[CH2:10]([O:12][C:13](=[O:37])[NH:14][C:15]1[C:20]([O:21][CH3:22])=[CH:19][C:18]([CH2:23][C:24]2[C:25]([NH2:26])=[N:8][C:7]([NH2:9])=[N:6][CH:33]=2)=[CH:17][C:16]=1[O:35][CH3:36])[CH3:11]

Participants

5

Reactant 3

HCID 286947Carbonic acid-guanidine (1:1)HCID 5360545SodiumHCID 704180124-(3-Anilino-2-cyano-allyl)-2,6-dimethoxy carbanilic acid ethyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 360 mg. of sodium in 100 ml. of absolute ethanol was treated with 2.8 g. of guanidine carbonate and 2.0 g. of 4-(3-anilino-2-cyano-allyl)-2,6-dimethoxy carbanilic acid ethyl ester and boiled under reflux for 20 hours. The solution was diluted with 100 ml. of water and the alcohol removed under vacuum. After standing at room temperature for 1 hour, the precipitate was removed by filtration with suction, washed with water and dissolved in about 200 ml. of boiling ethanol. The solution was chromatographed on 100 g. of silica gel using ethanol/ethyl acetate (1:1) and there was obtained 4-[(2,4-diamino-5-pyrimidinyl)-methyl]-2,6-dimethoxy-carbanilic acid ethyl ester which, after recrystallization from ethanol, had a melting point of 228° C. (decomposition).

Workup

  1. temperatureunder reflux for 20 hours
  2. additionThe solution was diluted with 100 ml
  3. customof water and the alcohol removed under vacuum
  4. customthe precipitate was removed by filtration with suction
  5. washwashed with water
  6. dissolutiondissolved in about 200 ml
  7. customThe solution was chromatographed on 100 g

Sources & evidence

ORD record
ord-9f31679942244b82bae39d3d6c78abb8
Source dataset
uspto-grants-1985_05
Patent number
US04515948

Reaction notes

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