Sodium Carbonate → HCID 25062518, compound

HRID 1664533Notes

Reaction equation

HRID 1664533 reaction equation
Br[C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]3[C:12]([CH3:15])=[N:13][N:14]=[C:6]3[N:5]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:4]=2[N:3]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:15][C:12]1[N:7]2[C:8](=[O:11])[C:9]3[NH:10][C:2]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:3][C:4]=3[N:5]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:6]2=[N:14][N:13]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 25061712HCID 25061712, compound

Product 1

HCID 25062518HCID 25062518, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 7-bromo-3-methyl-9-pentyl-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one (100 mg, 0.30 mmol), phenylboronic acid (39.5 mg, 0.32 mmol), sodium carbonate (100 mg, 0.94 mmol) in water (2 ml) and 1,2-dimethoxyethane (20 ml) was added tetrakis(triphenylphosphine)-palladium(0) (200 mg, 0.10 mmol). The mixture was heated to reflux overnight. The reaction mixture was diluted with water and extracted with ethyl acetate three times. The combined organic layers were dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative LCMS to yield the desired product (16 mg, 16%). 1HNMR (400 MHz, CD3OD): δ 8.06 (m, 2H), 7.49 (m, 3H), 4.38 (t, J=8.0 Hz, 2H), 2.83 (s, 3H), 1.95 (m, 2H), 1.42 (m, 4H), 0.92 (m, 3H). LCMS calculated for C18H21N6O (M+H): 337.2. found 337.2.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. extractionextracted with ethyl acetate three times
  4. dry with materialThe combined organic layers were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative LCMS

Sources & evidence

ORD record
ord-198297e23b444bcf8baffdeb3e94dfd3
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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