Diisopropylethylamine → Ethyl 1-ethyl-5-(2-phenylimidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylate

HRID 1958330Notes

Reaction equation

HRID 1958330 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH2:32]([O:34][C:35]([C:37]1[CH:41]=[N:40][N:39]([CH2:42][CH3:43])[C:38]=1[C:44]([OH:46])=O)=[O:36])[CH3:33].[C:47]1([C:53]2[N:54]=[C:55]3[N:60]=[C:59]([NH2:61])[CH:58]=[CH:57][N:56]3[CH:62]=2)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CN(C=O)C.O>[CH2:32]([O:34][C:35]([C:37]1[CH:41]=[N:40][N:39]([CH2:42][CH3:43])[C:38]=1[C:44](=[O:46])[NH:61][C:59]1[CH:58]=[CH:57][N:56]2[CH:62]=[C:53]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[N:54]=[C:55]2[N:60]=1)=[O:36])[CH3:33]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 508783902-Phenylimidazo[1,2-A]pyrimidin-7-amineHCID 670418082-Ethyl-2H-pyrazole-3,4-dicarboxylic acid 4-ethyl ester

Product 1

HCID 53467806Ethyl 1-ethyl-5-(2-phenylimidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylateYield 13%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

TBTU (1.1 g) and diisopropylethylamine (1.1 g) were added to a solution of 2-ethyl-2H-pyrazole-3,4-dicarboxylic acid 4-ethyl ester (610 mg) in DMF (7 ml), and the mixture was stirred for 30 min at RT. 2-Phenyl-imidazo[1,2-a]pyrimidin-7-ylamine (example 1, step 1, 725 mg) was added to the light yellow solution, and the mixture was stirred over the weekend at RT. Water (15 ml) was added, and the mixture was stirred for an additional 15 min. For purification, the precipitate was suspended in DMF (5 ml) and water (10 ml), and filtered; this process was repeated 4 times. The thus obtained title compound (150 mg, 13%) was dried under vacuum.

Workup

  1. stirringthe mixture was stirred over the weekend at RT
  2. stirringthe mixture was stirred for an additional 15 min
  3. customFor purification
  4. filtrationwater (10 ml), and filtered

Sources & evidence

ORD record
ord-fc1bbf507ec943cdbbac17e390bf1a27
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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