Acetonitrile → HCID 25254933, compound

HRID 1365820Notes

Reaction equation

HRID 1365820 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:5]2[S:10][C:9]([C:11]3[N:12]=[CH:13][S:14][CH:15]=3)=[N:8][C:6]=2[N:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:28](#[N:30])[CH3:29]>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:19]1[CH2:20][CH2:21][N:16]([C:4]2[C:5]3[S:10][C:9]([C:11]4[N:12]=[CH:13][S:14][CH:15]=4)=[N:8][C:6]=3[N:7]=[C:2]([C:29]3[CH:28]=[N:30][C:2]([NH2:7])=[N:3][CH:4]=3)[N:3]=2)[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 6342Acetonitrile2×HCID 10340Sodium CarbonateHCID 86630082HCID 86630082, compound

Product 1

HCID 25254933HCID 25254933, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

5-Chloro-7-morpholino-2-(thiazol-4-yl)thiazolo[4,5-d]pyrimidine, 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 130° C. for 15 minutes. Acetonitrile was added and the solution was filtered. The resulting organic layer was purified by reverse phase silica gel chromatography to give the product 138. MS data: (ESI+): MH+ 399.

Workup

  1. customThe solution was microwaved at 130° C. for 15 minutes
  2. filtrationthe solution was filtered
  3. customThe resulting organic layer was purified by reverse phase silica gel chromatography

Sources & evidence

ORD record
ord-03334cb1066d483fa31e0ed77c032eef
Source dataset
uspto-grants-2011_02
Patent number
US07893059B2

Reaction notes

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