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

HRID 869113Notes

Reaction equation

HRID 869113 reaction equation
[NH2:1][C:2]1[C:14]([C:15]([O:17]CC=C)=[O:16])=[C:5]2[N:6]=[C:7]([C:10]([F:13])([F:12])[F:11])[CH:8]=[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:14]([C:15]([OH:17])=[O:16])=[C:5]2[N:6]=[C:7]([C:10]([F:13])([F:11])[F:12])[CH:8]=[CH:9][N:4]2[N:3]=1

Participants

5

Reactant 2

HCID 12752PhenylsilaneHCID 90417814Allyl 2-amino-5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

Product 1

HCID 904168892-Amino-5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acidYield 56.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Allyl 2-amino-5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate 4a (240 mg, 0.8385 mmol) and phenylsilane (181.5 mg, 206.7 μL, 1.677 mmol) were dissolved in dry DCM (6 mL). Pd(PPh3)4 (38.76 mg, 0.03354 mmol) was added and the resulting solution was stirred at RT for 2 hrs. The suspension was filtered and the collected solid was washed with DCM (3×1 mL). The solid was dried under vacuum at 40° C. to yield compound 5a (117 mg, 56%).

Workup

  1. filtrationThe suspension was filtered
  2. washthe collected solid was washed with DCM (3×1 mL)
  3. customThe solid was dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-aab874c5e59948c59ab3e5375e409aeb
Source dataset
uspto-grants-2015_03
Patent number
US08969360B2

Reaction notes

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