Dimethylformamide → HCID 86669002, compound

HRID 2366236Notes

Reaction equation

HRID 2366236 reaction equation
N[N:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[N:4][CH2:3]1.[H-].[Na+].[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=1[C:19]1[S:20][C:21]2[C:26](S(C)(=O)=O)=[N:25][CH:24]=[N:23][C:22]=2[N:31]=1.C[N:33](C=O)C>>[Cl:8][C:5]1[N:4]=[CH:3][N:2]=[C:7]([NH:33][C:26]2[C:21]3[S:20][C:19]([C:13]4[C:12]([Cl:11])=[CH:17][CH:16]=[CH:15][C:14]=4[Cl:18])=[N:31][C:22]=3[N:23]=[CH:24][N:25]=2)[CH:6]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 66801598HCID 66801598, compoundHCID 66801895HCID 66801895, compound

Product 1

HCID 86669002HCID 86669002, compoundYield 71%

Conditions

Temperature
0 °C

Procedure

To a solution of 3-amino-6-chloropyrimidine (57 mg, 0.44 mmol) in DMF (2 mL) at 0° C. was added NaH (24 mg, 0.61 mmol). The reaction mixture was stirred at 0° C. for 10 minutes. A solution of 2-(2,6-dichlorophenyl)-7-(methylsulfonyl)thiazolo[4,5-d]pyrimidine (88 mg, 0.24 mmol) in DMF (1 mL) was then added at 0° C. The reaction mixture was warmed up to room temperature and stirred for 0.5 hour. The reaction was quenched with ice-water and extracted with EtOAc (3×25 mL). The combined organic extract was dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography eluting with 5-50% EtOAc/hexanes gradient to give the desired compound as a white solid (71 mg, 71%). 1H NMR (400 MHz, DMSO) δ 11.75 (s, 1H), 9.02 (s, 1H), 8.80 (s, 1H), 8.11 (s, 1H), 7.76 (d, J=8.3 Hz, 2H), 7.72-7.63 (m, 1H). LCMS (ESI) m/z: 490 [M+H+].

Workup

  1. temperatureThe reaction mixture was warmed up to room temperature
  2. stirringstirred for 0.5 hour
  3. customThe reaction was quenched with ice-water
  4. extractionextracted with EtOAc (3×25 mL)
  5. extractionThe combined organic extract
  6. dry with materialwas dried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with 5-50% EtOAc/hexanes gradient

Sources & evidence

ORD record
ord-47f6db5ca270412e95e754d97e6c4a51
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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