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

HRID 446299Notes

Reaction equation

HRID 446299 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 (used as a heat sink), added sodium metal (3.40 g, 148 mmol) slowly to methanol (180 mL). Stirred at RT for 30 minutes. Added guanidine hydrochloride (17.0 g, 182 mmol), stirred at RT for 30 minutes, added (E)-1-(2-chloropyridin-3-yl)-3-(dimethylamino)prop-2-en-1-one (12.0 g, 57.0 mmol), attached air condenser, and heated to 50° C. for 24 hours. Removed approximately half of the methanol by rotary evaporation. Filtered solids onto side-armed flask 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+H)+=206. Calc'd′206.63 for C9H7ClN4.

Workup

  1. customIn an argon purged 500 mL round bottom flask
  2. customplaced in an isopropanol bath
  3. temperatureheated to 50° C. for 24 hours
  4. customRemoved approximately half of the methanol
  5. customby rotary evaporation
  6. filtrationFiltered solids onto side-armed flask under vacuum
  7. washwashed with saturated NaHCO3 and H2O, air
  8. customdried

Sources & evidence

ORD record
ord-466c7bf5b8454c0dbf830906fe899eba
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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