Dimethylbarbituric acid → HCID 118024586, compound

HRID 1750549Notes

Reaction equation

HRID 1750549 reaction equation
C([N:4](CC=C)[CH:5]1[CH2:9][CH:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:7][CH:6]1[NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])C=C.CN1C(=O)CC(=O)N(C)C1=O>C(Cl)Cl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:4][CH:5]1[CH2:9][CH:8]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[CH2:7][CH:6]1[NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26]

Participants

5

Reactant 2

HCID 69860Dimethylbarbituric acidHCID 118024558HCID 118024558, compound

Product 1

HCID 118024586HCID 118024586, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of tert-butyl N-{2-[bis(prop-2-en-1-yl)amino]-4-[(4-methoxyphenyl)methoxy]cyclopentyl}carbamate (1.77 g, 4.25 mmol) in dry DCM (21 ml) was added 1,3-dimethyl-1,3-diazinane-2,4,6-trione (CAS number 769-42-6; 1.161 g, 7.44 mmol) and tetrakis(triphenylphosphane) palladium (0.113 g, 0.098 mmol). The reaction was stirred at 45° C. under an atmosphere of nitrogen for 3 hours. The reaction mixture was concentrated in vacuo and purified by SCX chromatography (2M ammonia in methanol) to afford the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by SCX chromatography (2M ammonia in methanol)

Sources & evidence

ORD record
ord-8fadad0112b1423ebd35c411c4b1bf69
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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