Tributylamine → HCID 178437204, compound

HRID 2304765Notes

Reaction equation

HRID 2304765 reaction equation
[CH3:1][C:2]1(C)C(C)(C)OB(C=C)O1.I[C:13]1[C:14]([NH2:20])=[N:15][C:16](=[O:19])[NH:17][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CCCC)CCCC)CCC>CO.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(Cl)(Cl)Cl>[CH:1]([C:13]1[C:14]([NH2:20])=[N:15][C:16](=[O:19])[NH:17][CH:18]=1)=[CH2:2]

Participants

8

Reactant 4

HCID 7622TributylamineHCID 11776TriphenylphosphineHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178509022HCID 178509022, compound

Product 1

HCID 178437204HCID 178437204, compoundYield 67.4%

Reagents, catalysts & solvents 3

HCID 6212ChloroformCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 887MethanolSolvent

Procedure

7.24 g of 4,4,5,5-tetramethyl-2-vinyl-1,3,2dioxaborolan (46.4 mmol), 10.00 g of 5-iodocytosine (42.2 mmol), 1.11 g of triphenylphosphine (14.2 mmol), 1.05 g of Pd2dba3.CHCl3 (1.1 mmol) and 15.1 ml tributylamine (63.3 mmol) in 200 ml of methanol were heated to reflux for 28 hours. After cooling the suspension to room temperature the crude product was filtered off and washed with methylene chloride. Crystallisation from boiling methanol gave 3.9 g (61%) of 5-vinylcytosine as white crystals, m.p. >290° C., MS (EI-MS): (m/z) 137 [M+H]+. 1H-NMR (250 MHz, D6-DMSO): 5.03 (1H, d, J=11.0), 5.45 (1H, d, J=17.3), 6.52 (1H, dd, J=17.3, 11.0), 6.8-7.2 (3H, br), 7.56 (1H, s).

Workup

  1. temperatureto reflux for 28 hours
  2. filtrationwas filtered off
  3. washwashed with methylene chloride
  4. customCrystallisation

Sources & evidence

ORD record
ord-f1fd83103e8a4e0fa2d77782ff49fdcc
Source dataset
uspto-grants-2002_08
Patent number
US06437118B1

Reaction notes

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