Dimethylamine → HCID 178508306, compound

HRID 750538Notes

Reaction equation

HRID 750538 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:28]2[O:29][CH:30]=[CH:31][CH:32]=2)[C:5]2[N:10]=[N:9][N:8]([CH2:11][C:12]3[CH:27]=[CH:26][C:15]4[N:16](C(OC(C)(C)C)=O)[N:17]=[N:18][C:14]=4[CH:13]=3)[C:6]=2[N:7]=1.C1COCC1.CNC>CO>[NH:16]1[C:15]2[CH:26]=[CH:27][C:12]([CH2:11][N:8]3[C:6]4[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([C:28]5[O:29][CH:30]=[CH:31][CH:32]=5)[C:5]=4[N:10]=[N:9]3)=[CH:13][C:14]=2[N:18]=[N:17]1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 21874651HCID 21874651, compound

Product 1

HCID 178508306HCID 178508306, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of tert-butyl 5-(5-amino-7-(2-furyl)-3H-triazolo[4,5-d]pyrimidin-3-yl)methyl-1H-benzotriazol-1-carboxylate (as a mixture with the 6-substituted regioisomer) (135 mg, 0.31 mmol) in MeOH (5 mL) and THF (5 mL was treated with 40% aqueous dimethylamine (0.176 mL, 1.56 mmol), refluxed for 25 min, concentrated in vacuo and the resulting solid triturated with ether, filtered, triturated with MeOH, filtered and dried to give the title compound (31 mg, 30%) as a yellow solid.

Workup

  1. temperaturerefluxed for 25 min
  2. concentrationconcentrated in vacuo
  3. customthe resulting solid triturated with ether
  4. filtrationfiltered
  5. customtriturated with MeOH
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-091dab5286404a9dbf4abfa80a6b0b8f
Source dataset
uspto-grants-2008_07
Patent number
US07405219B2

Reaction notes

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