Dimethylformamide → HCID 59592950, compound

HRID 2262194Notes

Reaction equation

HRID 2262194 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-d5a83d79d5e24a45967d102b876d9ccd
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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