Dimethylformamide → HCID 59592950, compound

HRID 2098769Notes

Reaction equation

HRID 2098769 reaction equation
[O:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].[H-].[Na+].Br[CH2:10][C:11]1[S:19][C:18]2[C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[N:16][C:15](Cl)=[N:14][C:13]=2[CH:12]=1.C[N:28]([CH:30]=O)C>>[NH:28]1[C:30]2[C:18](=[C:13]([C:15]3[N:16]=[C:17]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[C:18]4[S:19][C:11]([CH2:10][N:3]5[CH2:4][CH2:5][O:1][C:2]5=[O:6])=[CH:12][C:13]=4[N:14]=3)[CH:12]=[CH:11][CH:10]=2)[CH:17]=[N:16]1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 739492-OxazolidinoneHCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 59592950HCID 59592950, compound

Procedure

To a solution of 2-oxazolidinone (50 mg, 0.6 mmol) in DMF (2 mL) at 0° C. NaH (60% in mineral oil; 0.7 mmol) was added. After 15 minutes, 6-(bromomethyl)-2-chloro-4-morpholinothieno[3,2-d]pyrimidine 30 from Example 9 (200 mg, 0.6 mmol) in DMF (0.5 mL) was added and the reaction stirred 15 min. The reaction was quenched by the addition of saturated aqueous ammonium chloride. The aqueous layer was extracted with EtOAc. The combined organics were dried over Na2SO4, filtered, and concentrated in vacuo. 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 311 after reverse phase HPLC purification (6 mg). MS (Q1) 437 (M)+

Workup

  1. customat 0° C
  2. customThe reaction was quenched by the addition of saturated aqueous ammonium chloride
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9536d7e9d352434dbf5828a66c4e1e4e
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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