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

HRID 1653739Notes

Reaction equation

HRID 1653739 reaction equation
[H-].[Na+].[C:3](=[N:8][OH:9])([NH2:7])[CH2:4][CH2:5][CH3:6].[C:10]1([C:16]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:17]2[CH2:22][CH:21]([C:23](OC)=O)[CH2:20][N:19]=[CH:18]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[C:33]1([C:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:17]2[CH2:22][CH:21]([C:23]3[O:9][N:8]=[C:3]([CH2:4][CH2:5][CH3:6])[N:7]=3)[CH2:20][N:19]=[CH:18]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2794811N-HydroxybutyramidineHCID 100455711-Triphenylmethyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidine

Product 1

HCID 103208401-Triphenylmethyl-1,4,5,6-tetrahydro-5-(3-n-propyl-1,2,4-oxadiazol-5-yl)pyrimidineYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Prepared by a procedure similar to Example 9, where sodium hydride (60% dispersion in mineral oil 108 mg, 2.7 mmol) and butyramidoxime (276 mg, 2.7 mmol) were suspended in dry THF 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 (1.04 g, 2.7 mmol) was added, dissolved in dry THF and reflux continued 18 hours. The solvents were evaporated in vacuo and the residue was chromatographed (silica, chloroform/methanol, 9:1) to yield 1-triphenylmethyl-1,4,5,6-tetrahydro-5-(3-n-propyl-1,2,4-oxadiazol-5-yl)pyrimidine 785 mg (67%). This product was dissolved in triflouroacetic acid (2 ml), with stirring at room temperature for 24 hours. The yellow solution was then evaporated in vacuo, and the residue recrystallized from methanol/ether to yield 240 mg (43%) white crystals, mp 126°-128° C. identified by 300 MHz nmr.

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. customthe residue was chromatographed (silica, chloroform/methanol, 9:1)

Sources & evidence

ORD record
ord-8b087350f04b466dbd5b00f277ee203f
Source dataset
uspto-grants-1995_04
Patent number
US05403845

Reaction notes

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