Triethylamine → HCID 86723518, compound

HRID 2201283Notes

Reaction equation

HRID 2201283 reaction equation
[OH:1][C@H:2]([CH3:23])[CH2:3][N:4]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]2[C:6]([N:7]([CH3:22])[C:8](=[O:21])[N:9]([CH3:20])[C:10]2=[O:19])=[CH:5]1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33].C([O-])([O-])=O.[K+].[K+]>ClCCCl.CN(C1C=CN=CC=1)C.O>[CH3:31][S:32]([O:1][C@H:2]([CH3:23])[CH2:3][N:4]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]2[C:6]([N:7]([CH3:22])[C:8](=[O:21])[N:9]([CH3:20])[C:10]2=[O:19])=[CH:5]1)(=[O:34])=[O:33]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 86723517HCID 86723517, compound

Product 1

HCID 86723518HCID 86723518, compound

Reagents, catalysts & solvents 3

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

Procedure

To a solution of (R)-6-(2-hydroxypropyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (step 1) (925 mg, 2.95 mmol) in DCE (16 ml) was added triethylamine (2.05 ml, 14.8 mmol), DMAP (36 mg, 0.29 mmol) and methanesulfonyl chloride (1.15 ml, 14.8 mmol) at 0° C. and reaction stirred for 30 min. Solid K2CO3 was added to the reaction mixture and the resulting mixture 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 a yellow oil. The material was used without further purification.

Workup

  1. customreaction
  2. extractionextracted with DCM (3×20 ml) The
  3. concentrationconcentrated in vacuo
  4. customto yield a yellow oil
  5. customThe material was used without further purification

Sources & evidence

ORD record
ord-b7914579137647ccbd229a2073c6481e
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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