Guanidine Hydrochloride → 2,4-Diamino-5-(4-phenylbutyl)pyrimidine

HRID 440949Notes

Reaction equation

HRID 440949 reaction equation
CO[CH:3]=[C:4]([C:15]#[N:16])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.[NH2:18][C:19]([NH2:21])=[NH:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[NH2:21][C:19]1[N:20]=[C:15]([NH2:16])[C:4]([CH2:5][CH2:6][CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:3][N:18]=1

Participants

6

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 11430Potassium CarbonateHCID 541732801-Methoxy-2-cyano-6-phenyl-1-hexene

Product 1

HCID 153345612,4-Diamino-5-(4-phenylbutyl)pyrimidineYield 52.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 2.4 grams (0.011 mole) of 1-methoxy-2-cyano-6-phenyl-1-hexene, 4.2 grams (0.044 mole) of guanidine hydrochloride, and 7.6 grams (0.055 mole) of potassium carbonate in 40 mL of N,N-dimethylformamide was heated at 100° C. to 105° C. for about 20 hours. After this time the reaction mixture was diluted with 100 mL of water. The mixture was then extracted with two 100 mL portions of ethyl acetate. The combined extracts were washed with three 75 mL portions of an aqueous 10% lithium chloride solution. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The residue was subjected to column chromatography on basic alumina that was deactivated to Level III with water. Elution was accomplished with 1% to 3% methanol in methylene chloride. The appropriate fractions were combined and concentrated under reduced pressure, yielding 1.4 grams of 2,4-diamino-5-(4-phenylbutyl)pyrimidine; mp 126°-127° C. The NMR spectrum was consistent with the proposed product.

Workup

  1. extractionThe mixture was then extracted with two 100 mL portions of ethyl acetate
  2. washThe combined extracts were washed with three 75 mL portions of an aqueous 10% lithium chloride solution
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  6. washElution
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c17cee297f5b4926bde8e3f0035ca63a
Source dataset
uspto-grants-1996_05
Patent number
US05521192

Reaction notes

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