Sodium Carbonate → HCID 136247223, compound

HRID 1022454Notes

Reaction equation

HRID 1022454 reaction equation
Cl[C:2]1[NH:3][C:4](=[O:14])[C:5]2[CH:10]=[CH:9][N:8]([CH:11]3[CH2:13][CH2:12]3)[C:6]=2[N:7]=1.[F:15][C:16]([F:27])([F:26])[C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C(Cl)Cl.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>[CH:11]1([N:8]2[C:6]3[N:7]=[C:2]([C:20]4[CH:21]=[CH:22][C:17]([C:16]([F:27])([F:26])[F:15])=[CH:18][CH:19]=4)[NH:3][C:4](=[O:14])[C:5]=3[CH:10]=[CH:9]2)[CH2:13][CH2:12]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 136344413HCID 136344413, compound

Product 1

HCID 136247223HCID 136247223, compoundYield 55.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A microwave reaction vial was charged with 2-chloro-7-cyclopropyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (57 mg, 272 μmol), 4-(trifluoromethyl)phenylboronic acid (62.0 mg, 326 μmol), a 2M aqueous sodium carbonate solution (408 μL, 816 μmol), and tetrakis(triphenylphosphine)palladium(0) (15.7 mg, 13.6 μmol) in ethanol (1.09 mL). The reaction mixture was heated in a microwave at 150° C. for 8 min. At this time, the reaction was diluted with methylene chloride and was filtered through a pad of Celite®, washing with a 10% methanol/methylene chloride solution. The filtrate was dried over sodium sulfate, filtered, and concentrated in vacuo onto Celite®. Flash chromatography (12 g silica gel column, 25-50% ethyl acetate/hexanes) afforded 7-cyclopropyl-2-(4-trifluoromethyl-phenyl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one as a white solid (48.5 mg, 55.9%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.71-1.29 (m, 4H) 3.65 (d, J=4.90 Hz, 1H) 6.49 (d, J=3.58 Hz, 1H) 7.15 (d, J=3.39 Hz, 1H) 7.91 (d, J=8.67 Hz, 2H) 8.35 (d, J=7.91 Hz, 2H) 12.35 (br. s., 1H). LC-MS calcd. for C16H13F3N3O [(M+H)+] 320, obsd. 320.0.

Workup

  1. customA microwave reaction
  2. filtrationwas filtered through a pad of Celite®
  3. washwashing with a 10% methanol/methylene chloride solution
  4. dry with materialThe filtrate was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo onto Celite®

Sources & evidence

ORD record
ord-4737f8fe65cb481a955a1a39f115f88b
Source dataset
uspto-grants-2014_05
Patent number
US08722661B2

Reaction notes

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