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

HRID 2201208Notes

Reaction equation

HRID 2201208 reaction equation
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=[O:4])=[O:3].C(N(CC)CC)C.[Si:17]([O:24][CH2:25][CH:26](O)[CH2:27][N:28]1[C:36]([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[CH:38]=2)=[C:35]2[C:30]([N:31]([CH3:47])[C:32](=[O:46])[N:33]([CH3:45])[C:34]2=[O:44])=[CH:29]1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>ClCCCl.CN(C1C=CN=CC=1)C.O>[CH3:1][S:2]([O:5][CH:26]([CH2:27][N:28]1[C:36]([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[CH:38]=2)=[C:35]2[C:30]([N:31]([CH3:47])[C:32](=[O:46])[N:33]([CH3:45])[C:34]2=[O:44])=[CH:29]1)[CH2:25][O:24][Si:17]([C:20]([CH3:23])([CH3:21])[CH3:22])([CH3:18])[CH3:19])(=[O:4])=[O:3]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 867234486-(3-((tert-Butyldimethylsilyl)oxy)-2-hydroxypropyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 867234491-((tert-Butyldimethylsilyl)oxy)-3-(5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propan-2-yl methanesulfonate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Procedure

Methanesulfonic anhydride (0.679 g, 3.90 mmol) in 1,2-dichloroethane (3.0 mL) was added dropwise to a solution of DMAP (0.016 g, 0.130 mmol), triethylamine (0.544 ml, 3.90 mmol) and 6-(3-((tert-butyldimethylsilyl)oxy)-2-hydroxypropyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (0.6 g, 1.300 mmol) in 1,2-dichloroethane (10 mL) at 0° C. The mixture was warmed to room temperature and stirred for 2 hours, then diluted with water (10 mL). The phases were separated and the aqueous phase was extracted with DCM (3×10 mL). The combined organic extracts were dried over magnesium sulfate and evaporated under vacuum to afford the title compound.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with DCM (3×10 mL)
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-c0dbe5a093a9471ca6ade70bbd725e12
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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