HCID 67482843, compound → HCID 21897357, compound

HRID 719970Notes

Reaction equation

HRID 719970 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:16]=[N:15][C:14]([O:17][CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[CH:13][N:12]=1)C1C=CC=CC=1.[H][H]>O1CCCC1.CO.[Pd]>[O:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH:20]1[CH2:19][CH2:18][O:17][C:14]1[N:15]=[CH:16][C:11]([NH2:10])=[N:12][CH:13]=1

Participants

6

Reactant 2

HCID 67482843HCID 67482843, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21897357HCID 21897357, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of {5-[2-(tetrahydro-pyran-2-yl)-ethoxy]-pyrazin-2-yl}-carbamic acid benzyl ester (560 mg, 1.5 mmol) in tetrahydrofuran (5 mL) and methanol (15 mL) was treated with 10% palladium on activated carbon (110 mg) in methanol (5 mL). The reaction mixture was stirred under a positive pressure of hydrogen gas (balloon) at 25° C. for 2 h, at which time, thin layer chromatography indicated complete removal of the protection group. The reaction mixture was filtered and concentrated in vacuo to afford 5-[2-(tetrahydro-pyran-2-yl)-ethoxy]-pyrazin-2-ylamine as an oil which was used without further purification.

Workup

  1. customremoval of the protection group
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2196d28d02a04eaaa0f2acf004fffe33
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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