Sodium Carbonate → 2-Amino-4-furan-2-yl-6-isopropenyl-pyrimidine-5-carbonitrile

HRID 1355829Notes

Reaction equation

HRID 1355829 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](OS(C(F)(F)F)(=O)=O)[C:5]([C:16]#[N:17])=[C:4]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)[N:3]=1.[C:23](B(O)O)([CH3:25])=[CH2:24].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[NH2:1][C:2]1[N:3]=[C:4]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)[C:5]([C:16]#[N:17])=[C:6]([C:23]([CH3:25])=[CH2:24])[N:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10855372(Prop-1-en-2-yl)boronic acidHCID 86583747Trifluoromethanesulfonic acid 2-amino-5-cyano-6-furan-2-yl-pyrimidin-4-yl ester

Product 1

HCID 185073502-Amino-4-furan-2-yl-6-isopropenyl-pyrimidine-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

From trifluoromethanesulfonic acid 2-amino-5-cyano-6-furan-2-yl-pyrimidin-4-yl ester, isopropenylboronic acid, tetrakis(triphenylphosphine)palladium(O) and sodium carbonate in dioxane/water. EI-MS m/e (%): 226 (M+, 74), 225 ([M—H]+, 100).

Sources & evidence

ORD record
ord-78f482b887cd45f0a547c72756283758
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

Loading…