Carbon Tetrachloride → 3-Benzyloxy-7-methyl-2-(5-m-tolyl-[1,3,4]oxadiazol-2-yl)-pyrido[1,2-a]pyrimidin-4-one

HRID 536125Notes

Reaction equation

HRID 536125 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:12]2=[N:11][C:10]=1[C:21]([NH:23][NH:24][C:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=1)=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C.C(#N)C>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:12]2=[N:11][C:10]=1[C:21]1[O:22][C:25]([C:26]2[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=2)=[N:24][N:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 593929153-Methyl-benzoic acid N'-(3-benzyloxy-7-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carbonyl)-hydrazide

Product 1

HCID 581010333-Benzyloxy-7-methyl-2-(5-m-tolyl-[1,3,4]oxadiazol-2-yl)-pyrido[1,2-a]pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 8.3 (202 mg, 0.457 mmol), carbon tetrachloride (0.221 mL, 2.28 mmol) and triethylamine (0.165 mL, 1.19 mmol) were mixed with acetonitrile (10 mL). To this mixture was added triphenylphosphine (291 mg, 1.11 mmol) at room temperature. After being stirred at room temperature overnight, the reaction solution was diluted with ethyl acetate (100 mL), washed with aqueous saturated sodium bicarbonate (50 mL), water (50 mL) and brine (50 mL) successively, and then dried (Na2SO4). The crude product was subjected to flash chromatography (hexane-ethyl acetate 1:1) to give the desired compound

Workup

  1. washwashed with aqueous saturated sodium bicarbonate (50 mL), water (50 mL) and brine (50 mL) successively
  2. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-f921226c7968456f94f6392fae2b132f
Source dataset
uspto-grants-2014_10
Patent number
US08859563B2

Reaction notes

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