Carbon Tetrachloride → HCID 67251162, compound

HRID 2420985Notes

Reaction equation

HRID 2420985 reaction equation
[CH:1]1([C:4]([NH:6][NH:7][C:8]([C:10]2[C:11]([O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])=[N:12][C:13]([S:16][CH3:17])=[N:14][CH:15]=2)=[O:9])=O)[CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.C(Cl)(Cl)(Cl)Cl>C(#N)C>[CH:1]1([C:4]2[O:9][C:8]([C:10]3[C:11]([O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])=[N:12][C:13]([S:16][CH3:17])=[N:14][CH:15]=3)=[N:7][N:6]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 67251535HCID 67251535, compound

Product 1

HCID 67251162HCID 67251162, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

N′-cyclopropanecarbonyl-2-methylthio-4-(2-trimethylsilylethoxy)pyrimidine-5-carbohydrazide (9.27 g) obtained in Step 4 was dissolved in acetonitrile (250 mL), and triphenylphosphine (7.90 g) and triethylamine (7.0 mL) were added thereto. The mixture was stirred at 40° C. for 1 hour. Then, carbon tetrachloride (4.7 g) was added, and the mixture was stirred at 40° C. for 3 hours. After completion of the reaction was confirmed by thin-layer chromatography, the reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography. The fraction of the desired product was collected, and the solvent was evaporated under reduced pressure. Diethyl ether was added to the residue to precipitate crystals. The resulting crystals were collected by filtration and dried thoroughly under reduced pressure to give 5-(5-cyclopropyl[1,3,4]oxadiazol-2-yl)-4-(2-trimethylsilylethoxy)-2-methylthiopyrimidine [Compound (AA) in which —X—Y—Z— is —O—C(c-C3H5)═N—] (5.18 g, yield 59%).

Workup

  1. stirringthe mixture was stirred at 40° C. for 3 hours
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography
  4. customThe fraction of the desired product was collected
  5. customthe solvent was evaporated under reduced pressure
  6. additionDiethyl ether was added to the residue
  7. customto precipitate crystals
  8. filtrationThe resulting crystals were collected by filtration
  9. customdried thoroughly under reduced pressure

Sources & evidence

ORD record
ord-c9a0b7ff760048ed90fbd120089a7bcc
Source dataset
uspto-grants-2011_06
Patent number
US07956060B2

Reaction notes

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