Potassium tert-butoxide → 4,4-Dimethyl-tetrahydro-pyrimidin-2-one

HRID 629239Notes

Reaction equation

HRID 629239 reaction equation
Cl.C([O:6][C:7](=O)[NH:8][CH2:9][CH2:10][C:11]([NH2:14])([CH3:13])[CH3:12])(C)(C)C.CC([O-])(C)C.[K+]>C1COCC1>[CH3:12][C:11]1([CH3:13])[CH2:10][CH2:9][NH:8][C:7](=[O:6])[NH:14]1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 53422669tert-Butyl (3-amino-3-methylbutyl)carbamate hydrochloride

Product 1

HCID 584640534,4-Dimethyl-tetrahydro-pyrimidin-2-oneYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

(3.4 g, 14.3 mmol) (3-Amino-3-methyl-butyl)-carbamic acid tert-butyl ester hydrochloride was dissolved in THF (60 ml) and KOtBu (6.4 g, 57.1 mmol, 4 equiv.) was added. The mixture was stirred for 16 hours at 60° C. and evaporated then with isolute to dryness. The crude product was purified by flash chromatography by directly loading the residue onto a silica gel column and eluting with an ethyl acetate:methanol gradient 100:0 to 70:30. The desired 4,4-dimethyl-tetrahydro-pyrimidin-2-one (1.65 g, 90% yield) was obtained as a light yellow solid, MS: m/e=129.1 (M+H+).

Workup

  1. customevaporated
  2. customThe crude product was purified by flash chromatography
  3. washeluting with an ethyl acetate

Sources & evidence

ORD record
ord-a3c38226f6db456f8604f44470544d35
Source dataset
uspto-grants-2016_04
Patent number
US09315498B2

Reaction notes

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