2-Naphthalenecarboxaldehyde → 5-bromo-N-(naphthalen-2-ylmethyl)pyrazin-2-amine

HRID 559105Notes

Reaction equation

HRID 559105 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=O.[NH2:13][C:14]1[CH:19]=[N:18][C:17]([Br:20])=[CH:16][N:15]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C.C(O)(=O)C.ClCCl>[Br:20][C:17]1[N:18]=[CH:19][C:14]([NH:13][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[N:15][CH:16]=1

Participants

7

Reactant 3

HCID 62012-NaphthalenecarboxaldehydeHCID 5995392-Amino-5-bromopyrazineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 866143075-bromo-N-(naphthalen-2-ylmethyl)pyrazin-2-amineYield 48.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

2-Napthaldehyde (0.6 g, 3.84 mmol) and 2-amino-5-bromopyrazine (0.56 g, 3.201 mmol) were treated with Na(OAc)3BH (1.02 g, 4.802 mmol) in dichloroethane (15.0 mls) and acetic acid (0.5 mls) for 18 hours at room temperature. The mixture was diluted with dichloromethane, washed with 1.0 N NaOH, washed with brine, dried over MgSO4, and concentrated. Chromatography (SiO2, EtOAc: Hex, 1:1) gave 0.49 g 5-bromo-N-(naphthalen-2-ylmethyl)pyrazin-2-amine.

Workup

  1. washwashed with 1.0 N NaOH
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f19aac9b93a0424e8599658d08449247
Source dataset
uspto-grants-2011_11
Patent number
US08063057B2

Reaction notes

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