Sodium Carbonate → HCID 136344412, compound

HRID 1022449Notes

Reaction equation

HRID 1022449 reaction equation
Cl[C:2]1[NH:3][C:4](=[O:19])[C:5]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=2[N:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:26][C:27]([F:38])([F:37])[C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1>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.C(O)C>[F:26][C:27]([F:38])([F:37])[C:28]1[CH:33]=[CH:32][C:31]([C:2]2[NH:3][C:4](=[O:19])[C:5]3[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=3[N:7]=2)=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 136344411HCID 136344411, compound

Product 1

HCID 136344412HCID 136344412, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A microwave reaction vial was charged with 2-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (53.7 mg, 179 mop and ethanol (850 μL) (650 μL+200 μL rinse). The resulting mixture was treated with a 2M aqueous sodium carbonate solution (270 μL, 540 μmol), 4-(trifluoromethyl)phenylboronic acid (42.1 mg, 222 μmol), and tetrakis(triphenylphosphine)palladium(0) (13.2 mg, 11.4 μmol). The vial was tightly sealed and heated in a microwave at 150° C. for 8 min. At this time, the reaction was filtered through a pad of Celite®, rinsing copiously with methanol, and the filtrate was concentrated in vacuo onto Celite®. Flash chromatography (12 g silica gel column, 10-40% ethyl acetate/hexanes) afforded 2-(4-(trifluoromethyl)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one as a light yellow solid (47.7 mg, 65.0%). 1H NMR (300 MHz, DMSO-d6) δ ppm −0.13 (s, 9H) 0.85 (t, J=8.10 Hz, 2H) 3.56 (t, J=8.10 Hz, 2H) 5.58 (s, 2H) 6.59 (d, J=3.39 Hz, 1H) 7.34 (d, J=3.39 Hz, 1H) 7.90 (d, J=7.91 Hz, 2H) 8.36 (d, J=8.29 Hz, 2H) 12.45 (s, 1H). LC-MS calcd. for C19H23F3N3O2Si [(M+H)4] 410, obsd. 410.1.

Workup

  1. customA microwave reaction
  2. customThe vial was tightly sealed
  3. filtrationAt this time, the reaction was filtered through a pad of Celite®
  4. washrinsing copiously with methanol
  5. concentrationthe filtrate was concentrated in vacuo onto Celite®

Sources & evidence

ORD record
ord-5221c199572343b6afcb1109c36dd9ad
Source dataset
uspto-grants-2014_05
Patent number
US08722661B2

Reaction notes

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