Guanidine Hydrochloride → 5-[(4-methoxy-3-phenylmethoxyphenyl)methyl]pyrimidine-2,4-diamine

HRID 127924Notes

Reaction equation

HRID 127924 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[C:12](C#N)=[CH:13][CH2:14][NH:15]C1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:30][C:31]([NH2:33])=[NH:32].[CH3:34][O-].[Na+]>C(O)C>[NH2:32][C:31]1[N:33]=[C:14]([NH2:15])[C:13]([CH2:12][C:11]2[CH:24]=[CH:25][C:26]([O:27][CH3:28])=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:10]=2)=[CH:34][N:30]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 54197329HCID 54197329, compound

Product 1

HCID 114505255-[(4-methoxy-3-phenylmethoxyphenyl)methyl]pyrimidine-2,4-diamineYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

75 Grams (0.5 mole) of crude 3-benzyloxy-4-methoxy-β-cyano-N-phenylcinnamylamine is added to a suspension made by stirring 40 g (0.42 mole) of guanidine hydrochloride with 27.5 g (0.51 mole) of sodium methoxide in 320 ml of ethanol. The reaction mixture is stirred and heated at reflux for 1.5 hr., after which the mixture becomes quite thick. An additional 320 ml of ethanol is added, and the refluxing is continued for a total of 20 hr. Most of the ethanol is removed by vacuum distillation, the resulting residue is stirred with 1500 ml of water and washed well with water. The crude moist product is digested with 250 ml of hot ethanol, cooled, filtered, and washed with ethanol and with water to yield 55 g (81%) of 2,4-diamino-5-(3-benzyloxy-4-methoxybenzyl)pyrimidine, m.p. 210°-212°.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.5 hr
  3. customis continued for a total of 20 hr
  4. customMost of the ethanol is removed by vacuum distillation
  5. stirringthe resulting residue is stirred with 1500 ml of water
  6. washwashed well with water
  7. temperaturecooled
  8. filtrationfiltered
  9. washwashed with ethanol and with water

Sources & evidence

ORD record
ord-987e068ecaa3415f802f3d359bf7b64e
Source dataset
uspto-grants-1981_03
Patent number
US04258045

Reaction notes

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