Imidazole → HCID 59593033, compound

HRID 2262195Notes

Reaction equation

HRID 2262195 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][N:21]=[CH:20]1.C([O-])([O-])=O.[K+].[K+].C[N:31]([CH:33]=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:33]5[C:10]=4[CH:9]=[N:8][NH:31]5)=[N:6][C:5]=3[CH:4]=2)[CH:23]=[CH:22][N:21]=[CH:20]1

Participants

5

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 59593033HCID 59593033, compound

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 imidazole (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 312 after reverse phase HPLC purification (32 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-5a3593468e004a1e89d7fe5399601cb0
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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