Dimethyl Sulfoxide → HCID 131709885, compound

HRID 1579314Notes

Reaction equation

HRID 1579314 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[C:5]1[C:10](OCC)=[CH:9][C:8]([CH2:14][C:15]([C:23]#N)=[CH:16][N:17]2CCOCC2)=[CH:7][C:6]=1OCC)[CH3:2].[C:29](=[O:32])(O)O.[NH2:33][C:34]([NH2:36])=[NH:35].[CH3:37][CH2:38][O-:39].[Na+].[CH3:41]S(C)=O>>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[C:7]([O:39][CH2:38][CH3:37])[C:8]([CH2:14][C:15]2[C:16]([NH2:17])=[N:35][C:34]([NH2:36])=[N:33][CH:23]=2)=[C:9]([O:32][CH2:29][CH3:41])[CH:10]=1)=[O:28])[CH3:2]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 286947Carbonic acid-guanidine (1:1)HCID 2723922Sodium ethoxideHCID 54122772HCID 54122772, compound

Product 1

HCID 131709885HCID 131709885, compound

Procedure

A mixture of 1.94 g. of 4-(2-cyano-3-morpholinoallyl)-2,6-diethoxy-benzoic acid ethyl ester, 3.6 g. of guanidine carbonate and 1.36 g. of sodium ethylate in 20 ml. of absolute dimethylsulfoxide are stirred for 20 hours at 120°. After the addition of 200 ml. of water, the mixture is extracted with two 200 ml. portions of ethyl acetate. The ethyl acetate phase is washed twice with 50 ml. of water, dried over magnesium sulfate and evaporated under vacuum. The residue is chromatographed with ethyl acetate/methanol (4:1) on 40 g. of Kieselgel, whereby there is obtained α-(2,4-diamino-5-pyrimidinyl)-2,6-diethoxy-p-toluic acid ethyl ester having a m.p. of 197°-199°.

Workup

  1. additionA mixture of 1.94 g
  2. additionAfter the addition of 200 ml
  3. extractionof water, the mixture is extracted with two 200 ml
  4. washThe ethyl acetate phase is washed twice with 50 ml
  5. dry with materialof water, dried over magnesium sulfate
  6. customevaporated under vacuum
  7. customThe residue is chromatographed with ethyl acetate/methanol (4:1) on 40 g

Sources & evidence

ORD record
ord-9260a9b24e604d8cbc57c160e8a1d44b
Source dataset
uspto-grants-1976_01
Patent number
US03931181

Reaction notes

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