Sodium hydride → 1-Triphenylmethyl-1,4,5,6-tetrahydro-5-(3-methyl-1,2,4-oxadiazol-5-yl)pyrimidine

HRID 1681878Notes

Reaction equation

HRID 1681878 reaction equation
[H-].[Na+].[C:3](=[N:6][OH:7])([NH2:5])[CH3:4].[C:8]1([C:14]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:15]2[CH2:20][CH:19]([C:21](OC)=O)[CH2:18][N:17]=[CH:16]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[C:31]1([C:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:15]2[CH2:20][CH:19]([C:21]3[O:7][N:6]=[C:3]([CH3:4])[N:5]=3)[CH2:18][N:17]=[CH:16]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 30926N-HydroxyacetamidineHCID 100455711-Triphenylmethyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidine

Product 1

HCID 100244281-Triphenylmethyl-1,4,5,6-tetrahydro-5-(3-methyl-1,2,4-oxadiazol-5-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% dispersion in mineral oil 26 mg, 0.65 mmol) and acetamidoxime (48 mg, 0.65 mmol) were suspended in dry THF (4 ml) in an oven dried round bottom flask with stirring under nitrogen at 0° C. After 15 minutes stirring the ice bath was removed and the grey suspension refluxed 45 minutes to give a white suspension. 1-Triphenylmethyl-1,4,5,6-tetrahydro-5-methoxycarbonylpyrimidine (250 mg, 0.65 mmol) was added dissolved in dry THF (3 ml) and reflux continued 18 hours. The solvents were evaporated in vacuo and the residue taken up in water (10 ml). The aqueous suspension was extracted exhaustively with chloroform and the organics dried over MgSO4. After evaporation the organic residue was chromatographed (silica, chloroform/methanol, 9:1) to yield 93 mg (rf=0.26, 35%) white crystals, mp 72°-74° C. identified by 300 MHz nmr and ms m/z=408. Calculated: C 76.44, H 5.9, N 13.7; found: C 76.27, H 6.06, N 13.59.

Workup

  1. customdried round bottom flask
  2. stirringAfter 15 minutes stirring the ice bath
  3. customwas removed
  4. temperaturethe grey suspension refluxed 45 minutes
  5. customto give a white suspension
  6. temperaturereflux
  7. customThe solvents were evaporated in vacuo
  8. extractionThe aqueous suspension was extracted exhaustively with chloroform
  9. dry with materialthe organics dried over MgSO4
  10. customAfter evaporation the organic residue
  11. customwas chromatographed (silica, chloroform/methanol, 9:1)
  12. customto yield 93 mg (rf=0.26, 35%) white crystals, mp 72°-74° C.

Sources & evidence

ORD record
ord-5ad88c3bce824119bd428fa5b2bd1b39
Source dataset
uspto-grants-1992_12
Patent number
US05175166

Reaction notes

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