Isopropyl iodide → 7-isopropyl-5-methyl-3-(phenylamino)-2-(4-(pyridin-2-yl)benzyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 81402Notes

Reaction equation

HRID 81402 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[C:9]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)=[CH:15][CH:14]=3)[N:11]=[C:5]2[NH:4][C:3]1=[O:32].[CH:33](I)([CH3:35])[CH3:34].C([O-])([O-])=O.[Cs+].[Cs+]>CC(CC)=O>[CH:33]([N:4]1[C:5]2=[N:11][N:10]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)=[CH:17][CH:18]=3)[C:9]([NH:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[C:6]2[C:7](=[O:8])[N:2]([CH3:1])[C:3]1=[O:32])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 135581776HCID 135581776, compound

Product 1

HCID 426408837-isopropyl-5-methyl-3-(phenylamino)-2-(4-(pyridin-2-yl)benzyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Methylethylketone (1.2 mL) is added into a 0.5˜5 mL reaction vessel containing 5-methyl-3-(phenylamino)-2-(4-(pyridin-2-yl)benzyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (25 mg, 0.0589 mmol), isopropyl iodide (0.0707 mmol) and Cs2CO3 (0.0707 mmol). The sealed vessel is put onto a Biotage Microwave instrument and the microwave reaction is carried out at 140° C. for 1 hour. The obtained crude product is then purified by silica-gel flash chromatography to give pure product MS (ESI) m/z 467.2 [M+H]+.

Workup

  1. customthe microwave reaction
  2. customThe obtained crude product
  3. customis then purified by silica-gel flash chromatography
  4. customto give pure product MS (ESI) m/z 467.2 [M+H]+

Sources & evidence

ORD record
ord-0ab520f289574998b1fa296f666bf21d
Source dataset
uspto-grants-2014_09
Patent number
US08846693B2

Reaction notes

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