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

HRID 911108Notes

Reaction equation

HRID 911108 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 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 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 NaHCO3 and H2O, air
  9. customdried

Sources & evidence

ORD record
ord-ff3889234e7740d19ec8ca3e6cff3c1d
Source dataset
uspto-grants-2011_09
Patent number
US08022221B2

Reaction notes

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