Lawesson's reagent → HCID 86693571, compound

HRID 1485016Notes

Reaction equation

HRID 1485016 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=O)[N:11]([CH3:28])[CH:12]=[N:13][C:14]=1[C:15]1[O:16][C:17]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[N:18][N:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:10](=[S:39])[N:11]([CH3:28])[CH:12]=[N:13][C:14]=1[C:15]1[O:16][C:17]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[N:18][N:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 67446824HCID 67446824, compound

Product 1

HCID 86693571HCID 86693571, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Benzyloxy-6-[5-(4-fluoro-benzyl)-[1,3,4]oxadiazol-2-yl]-3-methyl-3H-pyrimidin-4-one was treated with 0.62 equiv of Lawesson's reagent at 80-85° C. in toluene for 5-7 h. TLC showed one major product formation with some substrate still present. Chromatography (eluted with 70%-90% EtOAc/hexane) gave ˜50% yield of the title compound.

Workup

  1. washChromatography (eluted with 70%-90% EtOAc/hexane)

Sources & evidence

ORD record
ord-77b2e4a66bf04da4be47b3b2efa3d3dd
Source dataset
uspto-grants-2016_08
Patent number
US09422282B2

Reaction notes

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