Dimethylbarbituric acid → HCID 67401263, compound

HRID 906641Notes

Reaction equation

HRID 906641 reaction equation
[CH2:1]([N:4](CC=C)[CH2:5][C:6]1[S:7][C:8]([S:11]([N:14]2[CH2:19][CH2:18][CH:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:16][CH2:15]2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)[CH:2]=[CH2:3].CN1C(=O)CC(=O)N(C)C1=[O:33].CCN(C(C)C)C(C)C.[C:50](Cl)(=O)[C:51]1C=CC=[C:53]([O:57][CH3:58])[CH:52]=1>C(Cl)Cl.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.CCOC(C)=O>[CH2:21]([O:20][CH:17]1[CH2:18][CH2:19][N:14]([S:11]([C:8]2[S:7][C:6]([CH2:5][NH:4][C:1](=[O:33])[C:2]3[CH:3]=[CH:50][CH:51]=[CH:52][C:53]=3[O:57][CH3:58])=[CH:10][CH:9]=2)(=[O:12])=[O:13])[CH2:15][CH2:16]1)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

8

Reactant 4

HCID 69860Dimethylbarbituric acidHCID 74374m-Anisoyl chlorideHCID 81531DiisopropylethylamineHCID 67401054HCID 67401054, compound

Product 1

HCID 67401263HCID 67401263, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 326a (134 mg, 0.3 mmol), 1,3 Dimethylbarbituric acid (94 mg, 0.6 mmol) and Tetrakis(triphenylphosphine)palladium (12 mg, 0.01 mmol) were stirred under Argon in 3 mL CH2Cl2. The reaction was followed by HPLC until all starting material disappeared. The crude was evaporated to dryness and taken up in dry THF. To this solution was added DIEA (230 ul, 1.5 mmol) and 3-anisoylchloride 0.3 mmol). The reaction was stirred for 3 h, EtOAc was added and the organic layer was extracted with NaHCO3 sat, HCl (0.1N) and brine. The dry solution was evaporated and purified by flash chromatography on silica gel using cyclohexane/EtOAc 7:3 as eluent. 326 was obtained as an oil (54 mg, 37%): H1 NMR (CDCl3) δ 7.43-7.25 (m, 4H), 7.15-7.05 (m, 2H), 6.60 (m, 1H), 4.83 (d, J=6.0 Hz, 2H), 3.86 (s, 3H), 3.35 (d, J=6.6, 2H), 335-3.23 (m, 3H), 2.95 (m, 2H), 1.94 (m, 2H), 1.86 (m, 2H), 1.70-1.50 (m, 5H), 1.30-1.20 (m, 8H), 0.87 (t, J=6.8, 3H), M/Z APCI: 495.2 (M+1).

Workup

  1. customThe crude was evaporated to dryness
  2. extractionthe organic layer was extracted with NaHCO3
  3. customThe dry solution was evaporated
  4. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-619504d190014e88b882fa3e5b8944a8
Source dataset
uspto-grants-2011_09
Patent number
US08012995B1

Reaction notes

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