Water → HCID 58834682, compound

HRID 218526Notes

Reaction equation

HRID 218526 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][NH:6][C:5]1=[O:10].C(N(CC)CC)C.[C:18]([Si:22](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:21])([CH3:20])[CH3:19].O>CN(C=O)C.CN(C1C=CN=CC=1)C>[Si:22]([O:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][NH:6][C:5]1=[O:10])([C:18]([CH3:21])([CH3:20])[CH3:19])([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 5528814853386-63-3

Product 1

HCID 58834682HCID 58834682, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

34.3 g (237 mmol) of 1-(2-hydroxyethyl)tetrahydropyrimidin-2(1H)-one (patent; Chem. Werke Huels; DE 1121617; 1962; Chem. Abstr.; EN; 56; 11601 g; 1962) are dissolved in 612 ml of DMF and admixed with 36.1 g (356 mmol) of triethylamine, 1.45 g (11.9 mmol) of DMAP and 85.0 g (309 mmol) of tert-butyl(chloro)diphenylsilane, and stirred at RT for 18 h. Then the mixture is added to 2000 ml of water and extracted three times with dichloromethane. The combined organic phases are washed twice with water and then dried over sodium sulfate. After filtration, the solvents are removed under reduced pressure. The residue is recrystallized from acetonitrile. This affords 71.9 g (78% of theory) of the desired compound.

Workup

  1. extractionextracted three times with dichloromethane
  2. washThe combined organic phases are washed twice with water
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvents are removed under reduced pressure
  6. customThe residue is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-bc471c3205d44ac2bb6d7b77b7ce7780
Source dataset
uspto-grants-2012_06
Patent number
US08198267B2

Reaction notes

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