Hydrochloric Acid → 3-decyl-1-benzyloxy-3,4,5,6-tetrahydro-lH-pyrimidin-2-one

HRID 974019Notes

Reaction equation

HRID 974019 reaction equation
[CH2:1]([NH:11][C:12]([NH:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10].[H-].[Na+].Br[CH2:26][CH2:27][CH2:28]Br.Cl>CN(C=O)C>[CH2:1]([N:11]1[CH2:28][CH2:27][CH2:26][N:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]1=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 14227196N-(9-decenyl)-N'-benzyloxyurea

Product 1

HCID 156754813-decyl-1-benzyloxy-3,4,5,6-tetrahydro-lH-pyrimidin-2-oneYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 9-decenyl isocyanate, prepared as in Example 18 above from 10.8 ml of 10-undecenoyl chloride in 1,2-dichloroethane (150 ml) at room temperature was added benzyloxyamine (7.2 g). After 20 minutes, the mixture was evaporated, hexane (50 ml) was added, and the mixture cooled to 0° C. The resulting solids were collected by filtration, to provide N-(9-decenyl)-N'-benzyloxyurea as a white solid (7.14 g, mp 53°-55° C.). To a stirred slurry of this urea (3.50 g, 11.65 mmol) in DMF (35 ml) at room temperature under nitrogen was added sodium hydride (490 mg of a 60% dispersion in oil). After one hour, 1,3-dibromopropane (1.45 ml) was added, and the reaction was stirred for two hours. The mixture was poured into 1% aqueous HCl (200 ml), and extracted twice with ether. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated. Purification by chromatography on silica gave 3-decyl-1-benzyloxy-3,4,5,6-tetrahydro-lH-pyrimidin-2-one as a colorless oil (1.92 g, 48% yield). Hydrogenolysis as in Example 2 above provided the title compound as a light magenta solid, after recrystallization from carbon tetrachloride, mp 45°-46° C.

Workup

  1. extractionextracted twice with ether
  2. washThe combined extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by chromatography on silica

Sources & evidence

ORD record
ord-3acfc565f3ac48bba33afd28ccee04a0
Source dataset
uspto-grants-1991_11
Patent number
US05066658

Reaction notes

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