Phenylsilane → 2-Amino-6-(cyanomethyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

HRID 1850672Notes

Reaction equation

HRID 1850672 reaction equation
[NH2:1][C:2]1[C:13]([C:14]([O:16]CC=C)=[O:15])=[C:5]2[N:6]=[CH:7][C:8]([CH2:10][C:11]#[N:12])=[CH:9][N:4]2[N:3]=1.C1([SiH3])C=CC=CC=1>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[C:13]([C:14]([OH:16])=[O:15])=[C:5]2[N:6]=[CH:7][C:8]([CH2:10][C:11]#[N:12])=[CH:9][N:4]2[N:3]=1

Participants

5

Reactant 2

HCID 12752PhenylsilaneHCID 86720890Allyl 2-amino-6-(cyanomethyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylate

Product 1

HCID 867208922-Amino-6-(cyanomethyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of allyl 2-amino-6-(cyanomethyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylate 4c (10.2 g, 39.65 mmol) in DCM (350 mL) was added phenylsilane (8.581 g, 9.773 mL, 79.3 mmol), followed by Pd(PPh3)4 (1.5 g, 1.298 mmol). The reaction was stirred at room temperature for 2 h. The reaction mixture was filtered and the solid was washed with DCM and dried under vacuum to provide 2-amino-6-(cyanomethyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid 5c as a yellow solid (8.61 g, 100% yield).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was washed with DCM
  3. customdried under vacuum

Sources & evidence

ORD record
ord-a4d92c5750984541a2cd8f116d8359ef
Source dataset
uspto-grants-2015_02
Patent number
US08957078B2

Reaction notes

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