Nitrogen → HCID 66953366, compound

HRID 1879942Notes

Reaction equation

HRID 1879942 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]2[C:22](I)=[CH:21][C:20]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:19][N:8]2[C:9](=[O:18])[C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:4].[CH:30]([O:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH2:31].N#N.O>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]2[C:22]([C:30]([O:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH2:31])=[CH:21][C:20]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:19][N:8]2[C:9](=[O:18])[C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:4]

Participants

8

Reactant 4

HCID 947NitrogenHCID 962WaterHCID 8108Butyl vinyl etherHCID 66953506HCID 66953506, compound

Product 1

HCID 66953366HCID 66953366, compoundYield 58.9%

Reagents, catalysts & solvents 3

HCID 812191,3-Bis(diphenylphosphino)propaneCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

3-Benzyl-9-iodo-7-morpholin-4-yl-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylic acid methyl ester (1 g, 1.92 mmol), n-Butyl vinyl ether (961 mg, 9.59 mmol), 1,3-Bis(diphenylphosphino)propane (DPPP) (24 mg, 0.058 mmol), Pd(OAc)2 (11 mg, 0.048 mmol) were mixed in DMF (15 ml). The mixture was heated at 80° C. under the atmosphere of N2 overnight, after which water was added and then extracted with dichloromethane. The extracts were combined, washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography to give the desired product (540 mg, yield 54%).

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-f48ba8a686c6405a95ff5e6537cbbe82
Source dataset
uspto-grants-2012_11
Patent number
US08318732B2

Reaction notes

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