Acetonitrile → HCID 25254934, compound

HRID 1365822Notes

Reaction equation

HRID 1365822 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:5]2[S:10][C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[N:8][C:6]=2[N:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:29](#[N:31])[CH3:30]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[O:14]1[CH2:15][CH2:16][N:11]([C:9]2[S:10][C:5]3[C:4]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[N:3][C:2]([C:30]4[CH:29]=[N:31][C:2]([NH2:7])=[N:3][CH:4]=4)=[N:7][C:6]=3[N:8]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 57685409HCID 57685409, compound

Product 1

HCID 25254934HCID 25254934, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalyst2×HCID 962WaterSolvent

Procedure

5-Chloro-2,7-dimorpholinothiazolo[4,5-d]pyrimidine 79, 5-pyrimidine-2-amine boronic acid (1.2 eq), and trans-dichlorobis(triphenylphosphine)palladium(II) (0.1 eq) were slurried with equal parts 1M sodium carbonate (3 eq) and acetonitrile. The solution was microwaved at 150° C. for 10 minutes. An additionally 0.1 equivalents of trans-dichlorobis(triphenylphosphine)palladium(II) was added and the solution was microwaved an additional 10 minutes at 150° C. Water was added and the solution was filtered. The resulting precipitate was purified by reverse phase silica gel chromatography to give 139.

Workup

  1. customThe solution was microwaved at 150° C. for 10 minutes
  2. customthe solution was microwaved an additional 10 minutes at 150° C
  3. filtrationthe solution was filtered
  4. customThe resulting precipitate was purified by reverse phase silica gel chromatography

Sources & evidence

ORD record
ord-2e01ac758be6439fbe243c6902b52514
Source dataset
uspto-grants-2011_02
Patent number
US07893059B2

Reaction notes

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