Sodium hydride → HCID 83039773, compound

HRID 2278986Notes

Reaction equation

HRID 2278986 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][CH:8]1[CH2:13][CH2:12][O:11][C:10]([CH3:15])([CH3:14])[CH2:9]1)=[O:6].[H-].[Na+]>C1COCC1>[CH3:14][C:10]1([CH3:15])[CH2:9][CH:8]([N:7]2[CH2:2][CH2:3][NH:4][C:5]2=[O:6])[CH2:13][CH2:12][O:11]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 90426655HCID 90426655, compound

Product 1

HCID 83039773HCID 83039773, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A −20° C. solution of 1-(2-chloroethyl)-3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)urea (0.700 g, 2.98 mmol) in THF (15 mL), under Ar, was treated with NaH (60% in mineral oil, 0.298 g, 7.46 mmol), allowed to warm to RT as the cooling bath expired and stirred overnight. The mixture was cooled to 0° C., quenched with saturated NH4Cl, warmed to RT, treatd with brine, extracted with EtOAc (2×) and the combined organics were dried over MgSO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 1-(2,2-dimethyltetrahydro-2H-pyran-4-yl)imidazolidin-2-one as a white solid (155 mg, 26%). 1H NMR (400 MHz, DMSO-d6): δ 6.24 (s, 1 H), 3.85 (m, 1 H), 3.67-3.54 (m, 2 H), 3.26-3.13 (m, 4 H), 1.53-1.37 (m, 4 H), 1.14 (d, J=10.2 Hz, 6 H); MS (ESI) m/z: 199.2 (M+H+).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customquenched with saturated NH4Cl
  3. temperaturewarmed to RT
  4. extractiontreatd with brine, extracted with EtOAc (2×)
  5. dry with materialthe combined organics were dried over MgSO4
  6. concentrationconcentrated to dryness
  7. custompurified via silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-7908150ae2994e56829abc3019e105eb
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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