Dimethyl Sulfoxide → 2-(1-benzothien-3-ylmethyl)-5-(2-hydroxyethyl)-7-isobutyl-3-(1-methyl-1H-pyrrol-2-yl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 1181822Notes

Reaction equation

HRID 1181822 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][N:11]2[C:19]([C:20]3[N:21]([CH3:25])[CH:22]=[CH:23][CH:24]=3)=[C:18]3[C:13]([N:14]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:15](=[O:27])[NH:16][C:17]3=[O:26])=[N:12]2)=[CH:2]1.N12[CH2:42][CH2:41]CN=C1CCCCC2.BrCCBr.CS(C)=[O:49]>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][N:11]2[C:19]([C:20]3[N:21]([CH3:25])[CH:22]=[CH:23][CH:24]=3)=[C:18]3[C:13]([N:14]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:15](=[O:27])[N:16]([CH2:41][CH2:42][OH:49])[C:17]3=[O:26])=[N:12]2)=[CH:2]1

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 78391,2-DibromoethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 694271552-(1-benzothien-3-ylmethyl)-7-isobutyl-3-(1-methyl-1H-pyrrol-2-yl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Product 1

HCID 589810672-(1-benzothien-3-ylmethyl)-5-(2-hydroxyethyl)-7-isobutyl-3-(1-methyl-1H-pyrrol-2-yl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Conditions

Temperature
80 °C

Procedure

2-(1-benzothien-3-ylmethyl)-7-isobutyl-3-(1-methyl-1H-pyrrol-2-yl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione was dissolved in anhydrous dimethylsulfoxide and 1,8-diazabicyclo[5.4.0]undec-7-ene was added. 1,2-dibromoethane was added and the mixture was heated at 80° C. for 18 h. The crude reaction product was purified by semi-prep RPHPLC eluting with water/acetonitrile/trifluoroacetic acid mixtures. 477 (M+H).

Workup

  1. customThe crude reaction product
  2. customwas purified by semi-prep RPHPLC
  3. washeluting with water/acetonitrile/trifluoroacetic acid mixtures

Sources & evidence

ORD record
ord-ecf8e2dfb9ee4d3d8d22b31a34fdc127
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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