Guanidine Hydrochloride → 4-(2-Chloropyridin-3-yl)pyrimidin-2-amine

HRID 1408501Notes

Reaction equation

HRID 1408501 reaction equation
[Na].Cl.[NH2:3][C:4]([NH2:6])=[NH:5].[Cl:7][C:8]1[C:13]([C:14](=O)/[CH:15]=[CH:16]/N(C)C)=[CH:12][CH:11]=[CH:10][N:9]=1>CO>[Cl:7][C:8]1[C:13]([C:14]2[CH:15]=[CH:16][N:3]=[C:4]([NH2:6])[N:5]=2)=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 5360545SodiumHCID 161089731-(2-Chloropyridin-3-yl)-3-(dimethylamino)prop-2-en-1-one

Product 1

HCID 533963354-(2-Chloropyridin-3-yl)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In an argon purged 500 mL round bottom flask placed in an isopropanol bath, was added sodium metal (3.40 g, 148 mmol) slowly to methanol (180 mL). The mixture was stirred at room temperature (RT) for about 30 minutes. To this was added guanidine hydrochloride (12.0 mL, 182 mmol) and the mixture was stirred at RT for 30 minutes, followed by addition of (E)-1-(2-chloropyridin-3-yl)-3-(dimethylamino)prop-2-en-1-one (12.0 g, 57.0 mmol), attached air condenser, moved reaction to an oil bath, where it was heated to about 50° C. for 24 h. Approximately half of the methanol was evaporated under reduced pressure and the solids were filtered under vacuum, then washed with saturated sodium bicarbonate (NaHCO3) and H2O, air dried to yield 4-(2-chloropyridin-3-yl)pyrimidin-2-amine as off white solid. MS m/z=207 [M+1]+. Calc'd for C9H7ClN4: 206.63.

Workup

  1. customIn an argon purged 500 mL round bottom flask
  2. customplaced in an isopropanol bath
  3. stirringthe mixture was stirred at RT for 30 minutes
  4. customreaction to an oil bath
  5. temperaturewhere it was heated to about 50° C. for 24 h
  6. customApproximately half of the methanol was evaporated under reduced pressure
  7. filtrationthe solids were filtered under vacuum
  8. washwashed with saturated sodium bicarbonate (NaHCO3) and H2O, air
  9. customdried

Sources & evidence

ORD record
ord-80ab0cc678eb4328a3c749319253983d
Source dataset
uspto-grants-2014_12
Patent number
US08921367B2

Reaction notes

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