Pyrazolo[1,5-a]pyrimidine-3-carbonyl chloride → N-(5-(5-cyano-2-methoxyphenyl)-1-(2-((trimethylsilyl)methoxy)ethyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 1466629Notes

Reaction equation

HRID 1466629 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH2:17][CH2:18][O:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:6]=1[C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:10]#[N:11].[N:25]1[N:29]2[CH:30]=[CH:31][CH:32]=[N:33][C:28]2=[C:27]([C:34](Cl)=[O:35])[CH:26]=1>O1CCCC1>[C:10]([C:9]1[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:7]([C:6]2[N:5]([CH2:17][CH2:18][O:19][CH2:20][Si:21]([CH3:23])([CH3:22])[CH3:24])[N:4]=[CH:3][C:2]=2[NH:1][C:34]([C:27]2[CH:26]=[N:25][N:29]3[CH:30]=[CH:31][CH:32]=[N:33][C:28]=23)=[O:35])[CH:8]=1)#[N:11]

Participants

4

Reactant 2

HCID 19623233Pyrazolo[1,5-a]pyrimidine-3-carbonyl chlorideHCID 668506633-(4-amino-1-(2-((trimethylsilyl)methoxy)ethyl)-1H-pyrazol-5-yl)-4-methoxybenzonitrile

Product 1

HCID 66851089N-(5-(5-cyano-2-methoxyphenyl)-1-(2-((trimethylsilyl)methoxy)ethyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamideYield 140.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-(4-amino-1-(2-((trimethylsilyl)methoxy)ethyl)-1H-pyrazol-5-yl)-4-methoxybenzonitrile (717 mg, 2.08 mmol) in tetrahydrofuran (20 mL) was added to pyrazolo[1,5-a]pyrimidine-3-carbonyl chloride (262 mg, 1.45 mmol) in tetrahydrofuran (5 mL) at 0° C. After addition, the mixture was warmed to room temperature, and then stirred overnight at this temperature. The mixture was concentrated to give 1.0 g (98%) of N-(5-(5-cyano-2-methoxyphenyl)-1-(2-((trimethylsilyl)methoxy)ethyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide, which was carried forward without purification. LCMS (ESI) m+H=490.1.

Workup

  1. additionAfter addition
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-afbbfafd0794427da928ae4f986c57d1
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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