Water → HCID 15389941, compound

HRID 1081653Notes

Reaction equation

HRID 1081653 reaction equation
[C:1]([C:3]([CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([F:20])([F:19])[F:18])=[C:4](OC)[CH3:5])#[N:2].C(=O)(O)O.[NH2:25][C:26]([NH2:28])=[NH:27].O>CN(C)C(=O)C>[NH2:27][C:26]1[N:28]=[C:1]([NH2:2])[C:3]([CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:18])([F:20])[F:19])=[C:4]([CH3:5])[N:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 286947Carbonic acid-guanidine (1:1)HCID 54147962HCID 54147962, compound

Product 1

HCID 15389941HCID 15389941, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Under a nitrogen atmosphere, a stirred solution of 7.6 grams (0.027 mole) of 3-cyano-2-methoxy-6-(2-trifluoromethylphenyl)-2-hexene and 12.2 grams (0.068 mole) of guanidine carbonate in 35 mL of N,N-dimethylacetamide was heated at about 150° C. for 40 hours. After this time, the reaction mixture was poured into 300 mL of water. The resultant solid was collected by filtration, and was then slurried in 100 mL of diethyl ether. The solid was again collected by filtration and was subjected to column chromatography on silica gel. Elution was accomplished using 10% methanol in methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 3.4 grams of 2,4-diamino-5-[3-(2-trifluoromethylphenyl)propyl]-6-methyl-pyrimidine, mp 151°-158° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. filtrationThe resultant solid was collected by filtration
  2. filtrationThe solid was again collected by filtration
  3. washElution
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-14bd88c542e9417b883665c62fe79664
Source dataset
uspto-grants-1996_12
Patent number
US05587379

Reaction notes

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