Sodium Carbonate → 4-(5-(1h-Indazol-4-yl)-2-((4-(methylsulfonyl)piperazin-1-yl)methyl)thiazolo[5,4-d]pyrimidin-7-yl)morpholine

HRID 1365808Notes

Reaction equation

HRID 1365808 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[N:10]=[C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]3)[S:8][C:6]=2[N:7]=1.B(O)(O)[C:29]1[CH:37]=[CH:36][CH:35]=[C:34]2[C:30]=1[CH:31]=[N:32][NH:33]2.C(=O)([O-])[O-].[Na+].[Na+]>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.C(#N)C>[NH:33]1[C:34]2[C:30](=[C:29]([C:2]3[N:3]=[C:4]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[C:5]4[N:10]=[C:9]([CH2:11][N:12]5[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]5)[S:8][C:6]=4[N:7]=3)[CH:37]=[CH:36][CH:35]=2)[CH:31]=[N:32]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 441183101H-Indazole-4-boronic acidHCID 445416755-Chloro-2-((4-methylsulfonylpiperazin-1-yl)methyl)-7-morpholinothiazolo[5,4-d]pyrimidine

Product 1

HCID 252546144-(5-(1h-Indazol-4-yl)-2-((4-(methylsulfonyl)piperazin-1-yl)methyl)thiazolo[5,4-d]pyrimidin-7-yl)morpholine

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalyst2×HCID 6342AcetonitrileSolvent2×

Procedure

5-Chloro-2-((4-methylsulfonylpiperazin-1-yl)methyl)-7-morpholinothiazolo[5,4-d]pyrimidine, 1H-indazol-4-yl-4-boronic acid (1.2 eq), and trans-dichlorobis(triphenylphosphine)palladium(II) (0.1 eq) were combined in a solution of equal parts sodium carbonate aqueous solution (1M, 3 eq) and acetonitrile. The solution was microwaved at 130° C. for eighteen minutes. An additional 0.1 equivalents of trans-dichlorobis(triphenylphosphine)palladium(II) was added and the solution was microwaved at 130° C. for an additional twenty minutes. Acetonitrile was added and the solution was filtered. The organic layer was purified by reverse phase chromatography to give the off white solid of 129.

Workup

  1. customThe solution was microwaved at 130° C. for eighteen minutes
  2. customthe solution was microwaved at 130° C. for an additional twenty minutes
  3. filtrationthe solution was filtered
  4. customThe organic layer was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-84b5ce9f3c844da3af3aad6c2134c197
Source dataset
uspto-grants-2011_02
Patent number
US07893059B2

Reaction notes

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