Sodium Carbonate → HCID 136247182, compound

HRID 1022442Notes

Reaction equation

HRID 1022442 reaction equation
[CH2:1]([N:5]1[C:9]2[N:10]=[C:11](Cl)[NH:12][C:13](=[O:14])[C:8]=2[CH:7]=[CH:6]1)[CH2:2][CH:3]=[CH2:4].C(=O)([O-])[O-].[Na+].[Na+].[F:22][C:23]([F:34])([F:33])[C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=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>[CH2:1]([N:5]1[C:9]2[N:10]=[C:11]([C:27]3[CH:28]=[CH:29][C:24]([C:23]([F:34])([F:33])[F:22])=[CH:25][CH:26]=3)[NH:12][C:13](=[O:14])[C:8]=2[CH:7]=[CH:6]1)[CH2:2][CH:3]=[CH2:4]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 136344409HCID 136344409, compound2×

Product 1

HCID 136247182HCID 136247182, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A microwave reaction vial was charged with 7-but-3-enyl-2-chloro-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (Intermediate B) (96.1 mg, 430 μmol,), ethanol (1.6 mL), a 2M aqueous sodium carbonate solution (645 μL, 1.29 mmol), 4-(trifluoromethyl)phenylboronic acid (98.2 mg, 517 μmol), and tetrakis(triphenylphosphine)palladium(0) (27.2 mg, 23.5 μmol). The reaction was heated in a microwave at 150° C. for 68 min. The reaction was filtered through a pad of Celite®, rinsing with ethanol. The filtrate was concentrated in vacuo onto Celite®. Flash chromatography (12 g silica gel column, 10-30% ethyl acetate/hexanes) afforded 7-but-3-enyl-2-(4-trifluoromethyl-phenyl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (98.9 mg, 69.1%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.59 (q, J=6.66 Hz, 2H) 4.29 (t, J=6.88 Hz, 2H) 4.84-5.21 (m, 2H) 5.58-5.95 (m, 1H) 6.52 (d, J=3.20 Hz, 1H) 7.25 (d, J=3.20 Hz, 1H) 7.90 (d, J=8.29 Hz, 2H) 8.34 (d, J=7.91 Hz, 2H) 12.32 (s, 1H). LC-MS calcd. for C17H15F3N3O [(M+H)+] 334, obsd. 334.1.

Workup

  1. customA microwave reaction
  2. filtrationThe reaction was filtered through a pad of Celite®
  3. washrinsing with ethanol
  4. concentrationThe filtrate was concentrated in vacuo onto Celite®

Sources & evidence

ORD record
ord-3e75670757714213917ee22003e3c2a4
Source dataset
uspto-grants-2014_05
Patent number
US08722661B2

Reaction notes

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