Water → HCID 86679610, compound

HRID 577663Notes

Reaction equation

HRID 577663 reaction equation
[F:1][C:2]1[C:10]2[C:9]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=3)=[N:8][C:7]([NH:21][C:22]3[CH:26]=[CH:25][N:24]([CH3:27])[N:23]=3)=[N:6][C:5]=2[N:4]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:3]=1.[Cl-].[NH4+].O>CCOC(C)=O.C([O-])(O)=O.[Na+].[Zn]>[NH2:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[O:11][C:9]1[C:10]2[C:2]([F:1])=[CH:3][N:4]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:33])([CH3:34])[CH3:35])[C:5]=2[N:6]=[C:7]([NH:21][C:22]2[CH:26]=[CH:25][N:24]([CH3:27])[N:23]=2)[N:8]=1

Participants

7

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 86679608HCID 86679608, compound

Product 1

HCID 86679610HCID 86679610, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A reaction vial was charged with 5-fluoro-N-(1-methyl-1H-pyrazol-3-yl)-4-(3-nitrophenoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine (520 mg, 1.04 mmol), zinc dust (340 mg, 5.2 mmol), ammonium chloride (279 mg, 5.2 mmol), water (4 mL) and EtOAc (20 mL). The reaction mixture was capped and stirred at rt for 20 hrs. The reaction was diluted with EtOAc (100 mL) and saturated aqueous NaHCO3 (15 mL). The insoluble material was removed by filtration through Celite. The filtrate was separated, and the organic layer was washed with brine (10 mL), dried over Na2SO4 and evaporated to afford the title compound (394 mg, 81% yield) as a foam. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.52 (s, 1H) 7.45 (s, 1H) 7.26 (d, J=2.27 Hz, 1H) 7.14 (t, J=7.93 Hz, 1H) 6.49-6.59 (m, 2H) 6.46 (dd, J=7.93, 1.38 Hz, 1H) 6.30-6.43 (m, 1H) 5.50 (s, 2H) 5.32 (s, 2H) 3.75 (s, 3H) 3.56-3.67 (m, 2H) 0.89-0.98 (m, 2H) 0.00 (s, 9H). m/z (APCI+) for C22H28FN7O2Si 470.1 (M+H)+.

Workup

  1. customA reaction
  2. customThe reaction mixture was capped
  3. customThe insoluble material was removed by filtration through Celite
  4. customThe filtrate was separated
  5. washthe organic layer was washed with brine (10 mL)
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-2950b4aa49734fc08bf94ed041e9f2da
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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