Pyrazole → HCID 59593158, compound

HRID 2262204Notes

Reaction equation

HRID 2262204 reaction equation
Br[CH2:2][C:3]1[S:11][C:10]2[C:9]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:8][C:7](Cl)=[N:6][C:5]=2[CH:4]=1.[NH:19]1[CH:23]=[CH:22][CH:21]=[N:20]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:19]1([CH2:2][C:3]2[S:11][C:10]3[C:9]([N:12]4[CH2:17][CH2:16][O:15][CH2:14][CH2:13]4)=[N:8][C:7]([C:5]4[CH:4]=[CH:3][CH:2]=[C:21]5[C:22]=4[CH:23]=[N:19][NH:20]5)=[N:6][C:5]=3[CH:4]=2)[CH:23]=[CH:22][CH:21]=[N:20]1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 59593158HCID 59593158, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(bromomethyl)-2-chloro-4-morpholinothieno[3,2-d]pyrimidine 30 from Example 9 (90 mg, 0.3 mmol) in DMF (3 mL) was added pyrazole (18 mg, 0.3 mmol) and K2CO3 (50 mg, 0.4 mmol). The resulting solution stirred at room temperature overnight then was concentrated in vacuo. The residue was diluted with water and filtered. The crude product was utilized in a Suzuki coupling using General Procedure A with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7 to provide 325 after reverse phase HPLC purification (13 mg). MS (Q1) 418 (M)+

Workup

  1. concentrationthen was concentrated in vacuo
  2. additionThe residue was diluted with water
  3. filtrationfiltered

Sources & evidence

ORD record
ord-d8f5cbaf68dc4ff8b923b2eedacd1195
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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