Triethylamine → 1-((tert-Butyldimethylsilyl)oxy)-4-(4-chlorothiazol-2-yl)-4-(5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-7-yl)butan-2-yl methanesulfonate

HRID 2201260Notes

Reaction equation

HRID 2201260 reaction equation
CS([O:5][S:6]([CH3:9])(=[O:8])=[O:7])(=O)=O.[Si:10]([O:17][CH2:18][CH:19](O)[CH2:20][CH:21]([C:28]1[NH:29][C:30]([C:41]2[CH:46]=[CH:45][CH:44]=[C:43]([F:47])[CH:42]=2)=[C:31]2[C:36](=[O:37])[N:35]([CH3:38])[C:34](=[O:39])[N:33]([CH3:40])[C:32]=12)[C:22]1[S:23][CH:24]=[C:25]([Cl:27])[N:26]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].C(N(CC)CC)C>C(Cl)Cl>[CH3:9][S:6]([O:5][CH:19]([CH2:20][CH:21]([C:22]1[S:23][CH:24]=[C:25]([Cl:27])[N:26]=1)[C:28]1[NH:29][C:30]([C:41]2[CH:46]=[CH:45][CH:44]=[C:43]([F:47])[CH:42]=2)=[C:31]2[C:36](=[O:37])[N:35]([CH3:38])[C:34](=[O:39])[N:33]([CH3:40])[C:32]=12)[CH2:18][O:17][Si:10]([C:13]([CH3:16])([CH3:14])[CH3:15])([CH3:11])[CH3:12])(=[O:7])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 867235007-(4-((tert-Butyldimethylsilyl)oxy)-1-(4-chlorothiazol-2-yl)-3-hydroxybutyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 867235011-((tert-Butyldimethylsilyl)oxy)-4-(4-chlorothiazol-2-yl)-4-(5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-7-yl)butan-2-yl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonic anhydride (347 mg, 1.989 mmol) was added to a solution of 7-(4-((tert-butyldimethylsilyl)oxy)-1-(4-chlorothiazol-2-yl)-3-hydroxybutyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (590 mg, 0.995 mmol) and triethylamine (0.416 mL, 2.98 mmol) in DCM (30 mL). The mixture was stirred at room temperature 20 mins. The reaction was quenched with saturated NaHCO3(aq) and extracted with DCM (3×). The combined organic extracts were passed through a hydrophobic frit and evaporated under vacuum to afford the title compound as a crude material which was used directly.

Workup

  1. customThe reaction was quenched with saturated NaHCO3(aq)
  2. extractionextracted with DCM (3×)
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-ca0562a5139d4d1f83e451a2a2cfc038
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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