Dimethylamine → HCID 178508306, compound

HRID 733012Notes

Reaction equation

HRID 733012 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-ef1b162935b34b19b770ebbe781a7e63
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

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