Triethylamine → HCID 20458237, compound

HRID 544567Notes

Reaction equation

HRID 544567 reaction equation
Cl.[CH2:2]([O:9][CH2:10][CH2:11][CH2:12][C:13]([NH2:15])=[NH:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[C:24](=[CH2:27])[C:25]#[N:26]>CCO>[NH2:26][C:25]1[CH:24]=[CH:27][N:15]=[C:13]([CH2:12][CH2:11][CH2:10][O:9][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 701982-ChloroacrylonitrileHCID 204582074-(Benzyloxy)butanimidamide--hydrogen chloride (1/1)

Product 1

HCID 20458237HCID 20458237, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 4-benzyloxybutanamidine hydrochloride (14.6 g.) and triethylamine (33 g.) in EtOH (80 ml.) was added 2-chloroacrylonitrile (11.3 g.) and the solution was heated under reflux for 2 hours and then evaporated to dryness. The residue was partitioned between 10% aqueous HOAc (100 ml.) and EtOAc (200 ml.) and the EtOAc was reextracted with 10% v/v aqueous HOAc (2×100 ml.). The combined aqueous layers were basified with concentrated aqueous NaOH and extracted with EtOAc (3×75 ml.) and the EtOAc solution was washed with brine and dried to give 4-amino-2-(3-benzyloxypropyl)pyrimidine (9.8 g.). This amino-derivative was heated under reflux with 2,2,2-trifluoroethylisothiocyanate (10 g.) in acetonitrile (20 ml.) for 23 hours and the mixture evaporated to dryness. The residue was chromatographed on silica gel using CH2Cl2 containing 1% v/v MeOH as eluant to give 2-(3-benzyloxypropyl)-4-[3-(2,2,2-trifluoroethyl)thioureido]pyrimidine (10 g.).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 2 hours
  3. customevaporated to dryness
  4. customThe residue was partitioned between 10% aqueous HOAc (100 ml.) and EtOAc (200 ml.)
  5. extractionextracted with EtOAc (3×75 ml.)
  6. washthe EtOAc solution was washed with brine
  7. customdried

Sources & evidence

ORD record
ord-493ec2b0f746455180f8b2f3410884e4
Source dataset
uspto-grants-1984_05
Patent number
US04451463

Reaction notes

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