Triethylamine → 5-bromo-3-(6-methyl-1H-benzo[d]imidazol-2-yl)pyrazin-2-amine

HRID 1959335Notes

Reaction equation

HRID 1959335 reaction equation
[NH2:1][C:2]1[C:3]([C:9](O)=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.[CH3:12][C:13]1[CH:14]=[C:15]([NH2:20])[C:16]([NH2:19])=[CH:17][CH:18]=1.C(OP(C#N)(OCC)=O)C.C(N(CC)CC)C>COCCOC.CCOC(C)=O>[Br:8][C:5]1[N:4]=[C:3]([C:9]2[NH:20][C:15]3[CH:14]=[C:13]([CH3:12])[CH:18]=[CH:17][C:16]=3[N:19]=2)[C:2]([NH2:1])=[N:7][CH:6]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 103323,4-DiaminotolueneHCID 76257Diethyl cyanophosphonateHCID 185216003-Amino-6-bromopyrazine-2-carboxylic acid

Product 1

HCID 580842975-bromo-3-(6-methyl-1H-benzo[d]imidazol-2-yl)pyrazin-2-amineYield 46%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-amino-6-bromo-pyrazine-2-carboxylic acid (2.5 g, 11.47 mmol), 4-methylbenzene-1,2-diamine (1.401 g, 11.47 mmol), diethoxyphosphoryl-formonitrile (2.058 g, 1.871 mL, 12.62 mmol) and triethylamine (2.321 g, 3.197 mL, 22.94 mmol) was heated in DME (75.00 mL) at 170° C. in the microwave for 1 hour. The reaction mixture was diluted with EtOAc, filtered and washed with water and brine, dried over MgSO4 and concentrated to a brown solid. The mixture was slurried in DCM and treated with diethyl ether/petroleum ether. The resultant solid was washed with ether and dried to afford the product as an orange/brown solid (1.6 g, 46% Yield). MS (ES+) 305.

Workup

  1. filtrationfiltered
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to a brown solid
  5. additiontreated with diethyl ether/petroleum ether
  6. washThe resultant solid was washed with ether
  7. customdried

Sources & evidence

ORD record
ord-f4c3635df350404faf0e7c4c8a191f85
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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