Dimethylformamide → HCID 59592964, compound

HRID 2098780Notes

Reaction equation

HRID 2098780 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.[OH:19][C:20]1[NH:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=1.C([O-])([O-])=O.[K+].[K+].C[N:36]([CH:38]=O)C>>[NH:36]1[C:38]2[C:10](=[C:5]([C:7]3[N:8]=[C:9]([N:12]4[CH2:17][CH2:16][O:15][CH2:14][CH2:13]4)[C:10]4[S:11][C:3]([CH2:2][N:21]5[C:22]6[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=6[NH:24][C:20]5=[O:19])=[CH:4][C:5]=4[N:6]=3)[CH:4]=[CH:3][CH:2]=2)[CH:9]=[N:8]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholineHCID 178517141HCID 178517141, compound

Product 1

HCID 59592964HCID 59592964, 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 2-hydroxybenzimidazole (35 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)-1′-1-indazole 7 to provide 326 after reverse phase HPLC purification (3 mg). MS (Q1) 484 (M)+

Workup

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

Sources & evidence

ORD record
ord-f05abdaae0a5429cbc131035cb8ef187
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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