Potassium Iodide → 6-(3-((4-Methoxybenzyl)oxy)-2-(tritylthio)propyl)-1,3-dimethyl-5-(4-methylthiazol-2-yl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 2201225Notes

Reaction equation

HRID 2201225 reaction equation
[I-].[K+].[CH3:3][N:4]1[C:9]2=[CH:10][NH:11][C:12]([C:13]3[S:14][CH:15]=[C:16]([CH3:18])[N:17]=3)=[C:8]2[C:7](=[O:19])[N:6]([CH3:20])[C:5]1=[O:21].Cl[CH2:23][CH:24]([S:36][C:37]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:25][O:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(N(C)C)=O>[CH3:35][O:34][C:31]1[CH:30]=[CH:29][C:28]([CH2:27][O:26][CH2:25][CH:24]([S:36][C:37]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:23][N:11]2[C:12]([C:13]3[S:14][CH:15]=[C:16]([CH3:18])[N:17]=3)=[C:8]3[C:9]([N:4]([CH3:3])[C:5](=[O:21])[N:6]([CH3:20])[C:7]3=[O:19])=[CH:10]2)=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 86723460(1-Chloro-3-((4-methoxybenzyl)oxy)propan-2-yl)(trityl)sulfaneHCID 1363483951,3-dimethyl-5-(4-methylthiazol-2-yl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 867234616-(3-((4-Methoxybenzyl)oxy)-2-(tritylthio)propyl)-1,3-dimethyl-5-(4-methylthiazol-2-yl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

Potassium iodide (9.80 mg, 0.059 mmol) was added to a mixture of 1,3-dimethyl-5-(4-methylthiazol-2-yl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (Intermediate Nd) (81 mg, 0.294 mmol), (1-chloro-3-((4-methoxybenzyl)oxy)propan-2-yl)(trityl)sulfane (158 mg, 0.323 mmol) and cesium carbonate (191 mg, 0.587 mmol) in dimethylacetamide (2 ml). The mixture was stirred at 50° C. for 3 days. The reaction mixture was partitioned between water (20 ml) and ethyl acetate (20 ml), the phases were separated and the aqueous phase extracted with ethyl acetate (10 ml). The combined organic extracts were washed with brine (20 ml), dried over magnesium sulfate and evaporated under vacuum. Purification by chromatography on silica, eluting with 0-50% EtOAc/hexane, afforded the title compound.

Workup

  1. customThe reaction mixture was partitioned between water (20 ml) and ethyl acetate (20 ml)
  2. customthe phases were separated
  3. extractionthe aqueous phase extracted with ethyl acetate (10 ml)
  4. washThe combined organic extracts were washed with brine (20 ml)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under vacuum
  7. customPurification by chromatography on silica
  8. washeluting with 0-50% EtOAc/hexane

Sources & evidence

ORD record
ord-b7eafdb18def480a91270bd1532355a7
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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