Triethylamine → 3a,7a-dihydro-1H-benzo[d][1,2,3]triazol-1-yl 2-amino-5-(2-(dimethylamino)ethoxy)pyrazolo[1,5-a]pyrimidine-3-carboxylate

HRID 1850678Notes

Reaction equation

HRID 1850678 reaction equation
[NH2:1][C:2]1[C:16]([C:17]([OH:19])=[O:18])=[C:5]2[N:6]=[C:7]([O:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])[CH:8]=[CH:9][N:4]2[N:3]=1.CCN(CC)CC.CN(C(O[N:35]1[N:43]=[N:42][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN1C(=O)CCC1>[NH2:1][C:2]1[C:16]([C:17]([O:19][N:35]2[CH:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]3[N:42]=[N:43]2)=[O:18])=[C:5]2[N:6]=[C:7]([O:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])[CH:8]=[CH:9][N:4]2[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 904115212-Amino-5-(2-(dimethylamino)ethoxy)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

Product 1

HCID 904115813a,7a-dihydro-1H-benzo[d][1,2,3]triazol-1-yl 2-amino-5-(2-(dimethylamino)ethoxy)pyrazolo[1,5-a]pyrimidine-3-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a suspension of 2-amino-5-[2-(dimethylamino)ethoxy]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (80 mg, 0.3016 mmol) in NMP (1 mL) was added Et3N (37.24 mg, 51.29 μL, 0.3680 mmol). To the mixture was added TBTU (Boron Tetrafluoride Ion (1)) (109.0 mg, 0.3396 mmol) portionwise over a 5 minutes. The mixture was allowed to stir at room temperature for 20 minutes before being partitioned between ethylacetate and water. The aqueous layer was extracted twice with ethylacetate and the combined organic layers were washed with brine, dried (MgSO4), and concentrated in vacuo to afford the product 3a,7a-dihydro-1H-benzo[d][1,2,3]triazol-1-yl 2-amino-5-(2-(dimethylamino)ethoxy)pyrazolo[1,5-a]pyrimidine-3-carboxylate as an oil (92 mg, 80% yield).

Workup

  1. custombefore being partitioned between ethylacetate and water
  2. extractionThe aqueous layer was extracted twice with ethylacetate
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0f57e7d3d17e4d8683aca7db96a1ccb6
Source dataset
uspto-grants-2015_02
Patent number
US08957078B2

Reaction notes

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