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

HRID 1466626Notes

Reaction equation

HRID 1466626 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]([CH2:13][CH2:14][O:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:11]=[CH:10][C:9]=2[NH2:21])[CH:5]=[CH:6][CH:7]=1.[N:22]1[N:26]2[CH:27]=[CH:28][CH:29]=[N:30][C:25]2=[C:24]([C:31](Cl)=[O:32])[CH:23]=1>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]([CH2:13][CH2:14][O:15][CH2:16][Si:17]([CH3:18])([CH3:20])[CH3:19])[N:11]=[CH:10][C:9]=2[NH:21][C:31]([C:24]2[CH:23]=[N:22][N:26]3[CH:27]=[CH:28][CH:29]=[N:30][C:25]=23)=[O:32])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 19623233Pyrazolo[1,5-a]pyrimidine-3-carbonyl chlorideHCID 668518435-(3-bromophenyl)-1-(2-((trimethylsilyl)methoxy)ethyl)-1H-pyrazol-4-amine

Product 1

HCID 66850688N-(5-(3-bromophenyl)-1-(2-((trimethylsilyl)methoxy)ethyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamideYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 5-(3-bromophenyl)-1-(2-((trimethylsilyl)methoxy)ethyl)-1H-pyrazol-4-amine (533 mg, 1.45 mmol), in tetrahydrofuran (5 mL) was added of 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 742 mg (99%) of N-(5-(3-bromophenyl)-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=513.1.

Workup

  1. additionAfter addition
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-7f6d3763b1a64f1395d231d226052b2d
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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