Guanidine Hydrochloride → 2-(2-AMINOPYRIMIDIN-4-YL)PHENOL

HRID 1581783Notes

Reaction equation

HRID 1581783 reaction equation
[Na].C[O-].[Na+].Cl.[NH2:6][C:7]([NH2:9])=[NH:8].CN(C)[CH:12]=[CH:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[OH:22])=O>CO>[NH2:8][C:7]1[N:9]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[OH:22])[CH:13]=[CH:12][N:6]=1

Participants

6

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 2821907HCID 2821907, compoundHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 1357419292-(2-AMINOPYRIMIDIN-4-YL)PHENOLYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium (1.21 g, 52.6 mmol) is added to 200 ml methanol to prepare a solution of sodium methoxide. After addition of guanidine hydrochloride (12.41 g, 129.9 mmol) and 3-(dimethylamino)-1-(2-hydroxyphenyl)-2-propen-1-one (5.0 g, 26.15 mmol; J. Heterocyclic Chem., 14:345, 1977) the mixture is heated at reflux over night. The reaction solvent is removed under reduced pressure, and the residue treated with water. The resulting precipitate is collected by filtration and dried in vacuo to give 4.25 g of 2-amino-4-(2-hydroxyphenyl)pyrimidine (87%). This pyrimidine pre-cursor is reacted with (2S)-glycidyl 3-nitrobenzenesulfonate substantially as described for Epoxide 1 to give 2.05 g of the title epoxide (37.5%).

Workup

  1. temperatureis heated
  2. temperatureat reflux over night
  3. customThe reaction solvent is removed under reduced pressure
  4. additionthe residue treated with water
  5. filtrationThe resulting precipitate is collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-849581ac3f3949b296388333b415ad6e
Source dataset
uspto-grants-2004_05
Patent number
US06730792B2

Reaction notes

Loading…