Tert-Butylamine → HCID 118159215, compound

HRID 713233Notes

Reaction equation

HRID 713233 reaction equation
Cl[C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][N:10]=[CH:9][C:5]2=[N:6][C:7]=1[Cl:8].CCN(C(C)C)C(C)C.[C:22]([NH2:26])([CH3:25])([CH3:24])[CH3:23].[NH4+].[Cl-]>C(Cl)Cl>[C:22]([NH:26][C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][N:10]=[CH:9][C:5]2=[N:6][C:7]=1[Cl:8])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 231227312,3-Dichloropyrido[3,4-b]pyrazine

Product 1

HCID 118159215HCID 118159215, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combined 2,3-dichloropyrido[3,4-b]pyrazine (1 g, 5.00 mmol) and DIPEA (1.75 mL, 10.00 mmol) in DCM (10.00 mL) and cooled to 0° C. and added tert-butylamine (1.590 mL, 15.00 mmol) and stirred for 48 h. The reaction mixture was poured into saturated aqueous NH4Cl and extracted twice with EtOAc. The organic extracts were combined, filtered through MgSO4, and concentrated in vacuo. The residue was redissolved in EtOAc, filtered through a one inch plug of silica, washing with EtOAc, and concentrated gave N-(tert-butyl)-3-chloropyrido[3,4-b]pyrazin-2-amine (1.04 g, 88%).

Workup

  1. extractionextracted twice with EtOAc
  2. filtrationfiltered through MgSO4
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was redissolved in EtOAc
  5. filtrationfiltered through a one inch plug of silica
  6. washwashing with EtOAc
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fd17d9e2f7434692ba1702041aea7861
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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