Dimethylformamide → HCID 59592997, compound

HRID 2098771Notes

Reaction equation

HRID 2098771 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]=[N:22][CH:21]=[N: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]=[N:22][CH:21]=[N:20]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 59592997HCID 59592997, 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 1,2,4-triazole (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 313 after reverse phase HPLC purification (16 mg). MS (Q1) 419 (M)+

Workup

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

Sources & evidence

ORD record
ord-7f8fd0cd773e4599a25a5fa9ace241eb
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

Loading…