Toluene → HCID 54156118, compound

HRID 1856696Notes

Reaction equation

HRID 1856696 reaction equation
C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[Si]([O:21][C@H:22]([CH2:35][CH2:36][C:37]1[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=1)[C@H:23]([CH3:34])[O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)(C(C)(C)C)(C)C.Br[C:44]1[C:45]([O:52][CH3:53])=[N:46][C:47]([O:50][CH3:51])=[N:48][CH:49]=1>C(O)C.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>[CH3:51][O:50][C:47]1[N:46]=[C:45]([O:52][CH3:53])[C:44]([C:28]2[CH:27]=[CH:26][C:25]([O:24][C@H:23]([C@H:22]([OH:21])[CH2:35][CH2:36][C:37]3[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=3)[CH3:34])=[CH:30][CH:29]=2)=[CH:49][N:48]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2557195-Bromo-2,4-dimethoxypyrimidineHCID 54020751(1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-ylbutoxy]benzeneboronic acid

Product 1

HCID 54156118HCID 54156118, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

Toluene (4 ml), 2M aqueous sodium carbonate (0.5 ml), (1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-ylbutoxy]benzeneboronic acid (0.200 g, example 15f)), and tetrakis(triphenylphosphine)palladium(0) (0.020 g) were added to a solution of 5-bromo-2,4-dimethoxypyrimidine (0.209 g) in ethanol (1 ml). The mixture was heated at 120° C. for 4 hours.

Sources & evidence

ORD record
ord-fc7e987d58f543f1916c91bda7282b26
Source dataset
uspto-grants-2000_11
Patent number
US06143751

Reaction notes

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