Dimethylbarbituric acid → HCID 68312858, compound

HRID 1530720Notes

Reaction equation

HRID 1530720 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([CH:17]2[CH2:20][CH2:19][N:18]2CC=C)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1C(=O)CC(=O)N(C)C1=O>C(Cl)Cl.CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([CH:17]2[CH2:20][CH2:19][NH:18]2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 69860Dimethylbarbituric acidHCID 68312943HCID 68312943, compound

Product 1

HCID 68312858HCID 68312858, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-3-(1-allylazetidin-2-yl)piperidine-1-carboxylic acid benzyl ester (163 mg, 0.518 mmol) in DCM (10 mL) was added 1,3-dimethylbarbituric acid (243 mg, 1.56 mmol) and Pd(PPh3)4 (60 mg, 0.052 mmol). The mixture was stirred at RT for 64 h, then diluted with MeOH and loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 0.5M NH3/MeOH. Further purification by column chromatography (Si-PCC, gradient 3-15% 2M NH3/MeOH in DCM) afforded the title compound (126.5 mg, 89%) as a colourless oil. LCMS (Method B): RT1.99 & 2.07 min [M+H]+ 275.

Workup

  1. washThe cartridge was washed with MeOH
  2. washthe product eluted with 0.5M NH3/MeOH
  3. customFurther purification by column chromatography (Si-PCC, gradient 3-15% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-a5666b1bb62f4c45bd1fe74d0a3dd153
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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