Isoamyl Nitrite → 1-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-3-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 403493Notes

Reaction equation

HRID 403493 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:32])=[N:8][N:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]3[C:20]([CH2:30][CH3:31])=[N:21][N:22]4[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[N:24][C:23]=34)=[CH:14][CH:13]=2)[C:10]=1N)=[O:5])[CH3:2].C(ON=O)CC(C)C>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:32])=[N:8][N:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]3[C:20]([CH2:30][CH3:31])=[N:21][N:22]4[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[N:24][C:23]=34)=[CH:14][CH:13]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 683789025-amino-1-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-3-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

Product 1

HCID 683789781-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-3-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

5-Amino-1-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-3-methyl-H-pyrazole-4-carboxylic acid ethyl ester (16) (923 mg, 1.76 mmol) was dissolved in 15 ml of THF and after addition of isoamylnitrite (620 mg, 5.29 mmol) the reaction mixture was stirred for 12 h at 70° C. The reaction mixture was evaporated under reduced pressure and purified by chromatography (10-50% EtOAc in cyclohexane, 30 min) to afford a yellow solid.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. custompurified by chromatography (10-50% EtOAc in cyclohexane, 30 min)
  3. customto afford a yellow solid

Sources & evidence

ORD record
ord-35925b2f21c74fcb8c4daa7d6ffdef9e
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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