Reaction #325192

Reaction equation

3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

K2CO3

Iodocyclopentane

→

1-cyclopentyl-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Solvents

DMF

Conditions

Workup

1. 1
   Otherreaction
2. 2
   Otherreaction
3. 3
   workup.STIRRINGwas stirred for 2 hours
4. 4
   OtherSolid K2CO3 was removed by filtration
5. 5
   OtherSolvent was partially removed in vacuo
6. 6
   workup.ADDITIONSodium citrate (50 ml) was added
7. 7
   Otherreaction
8. 8
   Extractionwas extracted with EtOAc
9. 9
   ConcentrationOrganic phases concentrated in vacuo
10. 10
    Otherpurified
11. 11
    Otherto yield BA79

Procedure

3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA75, 100 mg, 0.386 mmol) was dissolved in DMF (10 ml). K2CO3 (250 mg, 1.54 mmol) was added and reaction was stirred at room temperature under an argon atmosphere. Iodocyclopentane (0.134 ml, 1.16 mmol) was added with a syringe and reaction was stirred for 2 hours. Solid K2CO3 was removed by filtration. Solvent was partially removed in vacuo. Sodium citrate (50 ml) was added and reaction was extracted with EtOAc. Organic phases concentrated in vacuo and purified using by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA79.

Source