Allyl Alcohol → 7-allyl-5-methyl-2-(1-naphthylmethyl)-3-(4-pyridinyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 1181797

Reaction equation

HRID 1181797 reaction equation
[CH2:1](O)[CH:2]=[CH2:3].CS(Cl)(=O)=O.CCN(C(C)C)C(C)C.[CH3:19][N:20]1[C:25](=[O:26])[C:24]2=[C:27]([C:41]3[CH:46]=[CH:45][N:44]=[CH:43][CH:42]=3)[N:28]([CH2:30][C:31]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[CH:34]=[CH:33][CH:32]=3)[N:29]=[C:23]2[NH:22][C:21]1=[O:47].C(=O)([O-])[O-].[Cs+].[Cs+].S([O-])(=O)(=O)C>C(Cl)Cl>[CH2:3]([N:22]1[C:23]2=[N:29][N:28]([CH2:30][C:31]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[CH:34]=[CH:33][CH:32]=3)[C:27]([C:41]3[CH:42]=[CH:43][N:44]=[CH:45][CH:46]=3)=[C:24]2[C:25](=[O:26])[N:20]([CH3:19])[C:21]1=[O:47])[CH:2]=[CH2:1]

Participants

8

Reactant 6

HCID 7858Allyl AlcoholHCID 10796Cesium carbonateHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 85257MethanesulfonateHCID 1363341135-methyl-2-(1-naphthylmethyl)-3-(4-pyridinyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Product 1

HCID 589809647-allyl-5-methyl-2-(1-naphthylmethyl)-3-(4-pyridinyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

Allyl alcohol (17.7 μL, 0.261 mmol) was dissolved in anh. CH2Cl2 (1 mL) and cooled to −5° C. To this was added methanesulfonyl chloride (20.2 ul, 0.261 mmol) followed by N,N′diisopropylethylamine (45.4 μl, 0.261 mmol). The mixture was stirred at low temperature for 2 h. Meanwhile, 5-methyl-2-(1-naphthylmethyl)-3-(4-pyridinyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (100 mg, 0.261 mmol) was suspended in anh. N,N′dimethylacetamide (2 mL) followed by addition of cesium carbonate (85 mg, 0.261 mmol). at room temperature for 1 h. To the mixture was added the preformed mesylate and the mixture was heated at 100 ° C. for 4 h. Reaction was partitioned between ethylacetate and water. The organic phase was washed with water, brine and dried over sodium sulfate and concentrated in vacuo. The crude product was purified by semi prep HPLC eluting with acetonitrile/water/TFA mixtures.

Workup

  1. waitat room temperature for 1 h
  2. temperaturethe mixture was heated at 100 ° C. for 4 h
  3. customReaction
  4. customwas partitioned between ethylacetate and water
  5. washThe organic phase was washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by semi prep HPLC
  9. washeluting with acetonitrile/water/TFA mixtures

Sources & evidence

ORD record
ord-afba3450833d4d57bf9669132e0b543d
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Linked notes

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