Guanidine Hydrochloride → 5-(naphthalen-2-ylmethyl)pyrimidine-2,4-diamine

HRID 279977Notes

Reaction equation

HRID 279977 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12](=[CH:15]NC1C=CC=CC=1)[C:13]#[N:14].C[O-].[Na+].Cl.[NH2:27][C:28]([NH2:30])=[NH:29]>C(O)C>[NH2:29][C:28]1[N:30]=[C:13]([NH2:14])[C:12]([CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[CH:15][N:27]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 67936478HCID 67936478, compound

Product 1

HCID 5166695-(naphthalen-2-ylmethyl)pyrimidine-2,4-diamineYield 51.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-(2-Naphthylmethyl)-3-anilinoacrylonitrile (6.65 g, 23.4 mmol) was dissolved in absolute ethanol (225 ml) and heated to reflux. A solution of sodium methylate (4.27 g, 79 mmol) in ethanol (75 ml) was mixed with guanidine hydrochloride (6.87 g, 72 mmol), filtered from salt, and added to the solution of 2-(2-naphthylmethyl)-3-anilinoacrylonitrile. The mixture was then refluxed for 8 hours, and allowed to stand at room temperature overnight. A yellow precipitate formed, which was isolated (2.66 g). An additional 1.33 g was obtained by concentration of the mother liquor. The combined fractions were recrystallized from absolute ethanol, yielding light cream colored 2,4-diamino-5-(2-naphthylmethyl)pyrimidine (3.0 g), m.p. 231°-233° C. Anal. Calcd. for C15H14N4 : C, 71.98; H, 5.64; N, 22.38. Found: C, 71.93; H, 5.68; N, 22.35.

Workup

  1. temperatureheated to reflux
  2. filtrationfiltered from salt
  3. additionadded to the solution of 2-(2-naphthylmethyl)-3-anilinoacrylonitrile
  4. temperatureThe mixture was then refluxed for 8 hours
  5. customA yellow precipitate formed
  6. customwhich was isolated (2.66 g)
  7. customAn additional 1.33 g was obtained by concentration of the mother liquor
  8. customThe combined fractions were recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-f4030fe02f784b93baa0238b94769fd5
Source dataset
uspto-grants-1986_05
Patent number
US04587341

Reaction notes

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