Triethylamine → HCID 86723443, compound

HRID 2201201Notes

Reaction equation

HRID 2201201 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([OH:31])[CH2:11][N:12]1[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:19]2[C:14]([N:15]([CH3:30])[C:16](=[O:29])[N:17]([CH3:28])[C:18]2=[O:27])=[CH:13]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41].C([O-])([O-])=O.[K+].[K+]>ClCCCl.CN(C1C=CN=CC=1)C.O>[CH3:39][S:40]([O:31][CH:10]([CH2:11][N:12]1[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:19]2[C:14]([N:15]([CH3:30])[C:16](=[O:29])[N:17]([CH3:28])[C:18]2=[O:27])=[CH:13]1)[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])(=[O:42])=[O:41]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 86723444HCID 86723444, compound

Product 1

HCID 86723443HCID 86723443, compound

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 6-(3-(tert-butyldimethylsilyloxy)-2-hydroxypropyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (step 2) (1 g, 2.25 mmol) in DCE (20 ml) was added triethylamine (1.57 ml, 11.27 mmol), DMAP (28 mg, 0.025 mmol) and methanesulfonyl chloride (0.89 ml, 11.3 mmol) at 0° C. and reaction stirred for 2 hours at RT. Solid K2CO3 was added to the reaction mixture and then it was diluted with water and extracted with DCM (3×20 ml). The organics were passed through a hydrophobic frit and concentrated in vacuo to yield the title compound as a brown oil which was used without further purification;

Workup

  1. customreaction
  2. extractionextracted with DCM (3×20 ml)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-73ed5871a6e64e73b5023c650d405add
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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