Tert-Butylamine → N-(tert-butyl)-5-chloro-2-methylpyrido[3,4-b]pyrazin-3-amine

HRID 1056246Notes

Reaction equation

HRID 1056246 reaction equation
Cl[C:2]1[N:7]=[C:6]2[C:8]([Cl:12])=[N:9][CH:10]=[CH:11][C:5]2=[N:4][C:3]=1[CH3:13].[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15]>CN1C(=O)CCC1.O>[C:14]([NH:18][C:2]1[N:7]=[C:6]2[C:8]([Cl:12])=[N:9][CH:10]=[CH:11][C:5]2=[N:4][C:3]=1[CH3:13])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 897821093,5-Dichloro-2-methylpyrido[3,4-b]pyrazine

Product 1

HCID 89781928N-(tert-butyl)-5-chloro-2-methylpyrido[3,4-b]pyrazin-3-amineYield 11.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

A glass microwave reaction vessel was charged with 3,5-dichloro-2-methylpyrido[3,4-b]pyrazine (110 mg, 0.51 mmol) and tert-butylamine (0.16 mL, 1.54 mmol) (Sigma Aldich) in NMP (1.0 mL). The reaction mixture was stirred and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 60° C. for 2 h. The mixture was diluted with water and extracted with DCM (30 mL×3). The combined organic layers was washed with water (30 mL×3) and dried (MgSO4), filtered and concentrated. The residue was purified by silica gel chromatography (10-30% EtOAc in Hexanes) to give N-(tert-butyl)-5-chloro-2-methylpyrido[3,4-b]pyrazin-3-amine (15 mg, 0.060 mmol, 11% yield). MS (ESI, pos. ion) m/z: 251.1 (M+1).

Workup

  1. customA glass microwave reaction vessel
  2. extractionextracted with DCM (30 mL×3)
  3. washThe combined organic layers was washed with water (30 mL×3)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (10-30% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-bfa02b2773c048bbbbcc61c4fbff8f14
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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