Water → HCID 22256028, compound

HRID 2117229Notes

Reaction equation

HRID 2117229 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].[H-].[Na+].Cl[CH2:9][C:10]1[N:11]=[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:13][CH:14]=1.O>CN1C(=O)N(C)CCC1.C1COCC1>[C:15]1([C:12]2[O:13][CH:14]=[C:10]([CH2:9][O:4][CH2:3][CH2:2][CH2:1][OH:5])[N:11]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 104421,3-PropanediolHCID 24758Sodium hydrideHCID 35511964-(Chloromethyl)-2-phenyl-1,3-oxazole

Product 1

HCID 22256028HCID 22256028, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
0 °C

Procedure

1,3-Propanediol (3.6 mL, 50 mmol) is dissolved in 10% DMPU in THF and cooled to 0° C. Sodium hydride is added portionwise (60%, 400 mg, 10 mmol). The contents are stirred for 10 min at 0° C., warmed to r.t. and stirred for another 10 min. 4-Chloromethyl-2-phenyl-oxazole (2.0 g, 10 mmol, EXAMPLE 21) is added, and the contents heated to 60° C. for 4 days. The reaction is cooled to r.t., poured into water (200 mL) and extracted with ethyl acetate (2×200 mL). The organic fractions were pooled and washed with brine (2×200 mL), dried over MgSO4, filtered and reduced under vacuum to an oil. The crude material was purified by flash chromatography (silica, 2% methanol in dichloromethane) to give the title compound. MS (ESI) 234 (M+H)+.

Workup

  1. temperaturewarmed to r.t.
  2. stirringstirred for another 10 min
  3. temperaturethe contents heated to 60° C. for 4 days
  4. temperatureThe reaction is cooled to r.t.
  5. extractionextracted with ethyl acetate (2×200 mL)
  6. washwashed with brine (2×200 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customThe crude material was purified by flash chromatography (silica, 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-45976e4a81a64a80aa4756a225b273c4
Source dataset
uspto-grants-2008_10
Patent number
USRE040558E1

Reaction notes

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