Formic Acid → HCID 66699794, compound

HRID 388085Notes

Reaction equation

HRID 388085 reaction equation
[C:1]1([C@H:7]([NH:9][C:10]2[C:15]([NH2:16])=[N:14][CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:18]1[N:23]=[C:22]([NH:24][C@@H:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH3:26])[C:21]([NH2:33])=[N:20][CH:19]=1.[CH:34](O)=[O:35]>[Pd]>[C:1]1([C@H:7]([N:9]2[C:10]3=[N:11][CH:12]=[CH:13][N:14]=[C:15]3[NH:16][C:34]2=[O:35])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:27]1([C@H:25]([NH:24][C:22]2[C:21]([NH2:33])=[N:20][CH:19]=[CH:18][N:23]=2)[CH3:26])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 66699794HCID 66699794, compoundHCID 72191063HCID 72191063, compound

Product 2

HCID 66699735HCID 66699735, compoundHCID 66699794HCID 66699794, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(R)-N2-(1-Phenylethyl)pyrazine-2,3-diamine. The title compound was prepared by dissolving (R)-6-bromo-N2-(1-phenylethyl)pyrazine-2,3-diamine (1.00 g, 3.37 mmol) in neat formic acid (15 mL), and adding 10% Pd/C (0.34 mmol). This solution was purged with hydrogen gas at 1 atm., and stirred for 4 hours at room temperature. Upon completion, the reaction was filtered through celite and concentrated. The crude material was purified using silica gel chromatography (0-10% methanol in dichloromethane). Clean fractions were combined and condensed to afford 0.65 g (3.03 mmol, 90%) of (R)-N2-(1-phenylethyl)pyrazine-2,3-diamine. MS (ESI) m/z 215.4 [M+1]+.

Workup

  1. customThis solution was purged with hydrogen gas at 1 atm.
  2. filtrationUpon completion, the reaction was filtered through celite
  3. concentrationconcentrated
  4. customThe crude material was purified
  5. customcondensed

Sources & evidence

ORD record
ord-63dfd0dc8f1f457095418315f949c164
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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