Ethanol → HCID 58930873, compound

HRID 388040Notes

Reaction equation

HRID 388040 reaction equation
[Cl-].[NH4+].C(O)C.O1CCCC1.[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[N:44]([CH2:45][O:46][CH2:47][CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50])[C:28]3[N:29]=[CH:30][N:31]=[C:32]([O:33][C:34]4[CH:39]=[CH:38][C:37]([N+:40]([O-])=O)=[C:36]([F:43])[CH:35]=4)[C:27]=3[CH:26]=2)=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[Fe].O>[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[N:44]([CH2:45][O:46][CH2:47][CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50])[C:28]3[N:29]=[CH:30][N:31]=[C:32]([O:33][C:34]4[CH:39]=[CH:38][C:37]([NH2:40])=[C:36]([F:43])[CH:35]=4)[C:27]=3[CH:26]=2)=[CH:21][CH:20]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 58930880HCID 58930880, compound

Product 1

HCID 58930873HCID 58930873, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

After adding 400 mg of iron powder, 1 g of ammonium chloride, 20 ml of ethanol, 10 ml of tetrahydrofuran and 10 ml of water to 470 mg of 6-(4-benzyloxyphenyl)-4-(3-fluoro-4-nitrophenoxy)-7-(trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine, the mixture was stirred at 85° C. for 3 hours. After returning it to room temperature, it was filtered with celite, and ethyl acetate and water were added to the filtrate for liquid separation and extraction. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, filtered with plug cotton, concentrated and subjected to NH silica gel column chromatography (hexane-ethyl acetate) to obtain 263 mg of the title compound.

Workup

  1. customto room temperature
  2. filtrationit was filtered with celite, and ethyl acetate and water
  3. additionwere added to the filtrate for liquid separation and extraction
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered with plug cotton
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f656b86ea36b470e84e04c59c25c6b24
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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