Triethylamine → HCID 86723514, compound

HRID 2201276Notes

Reaction equation

HRID 2201276 reaction equation
[OH:1][CH2:2][C@H:3]([N:25]1[C:33]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:32]2[C:27]([N:28]([CH3:43])[C:29](=[O:42])[N:30]([CH3:41])[C:31]2=[O:40])=[CH:26]1)[CH2:4][S:5][C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.[CH3:51][S:52](Cl)(=[O:54])=[O:53]>C(Cl)Cl>[CH3:51][S:52]([O:1][CH2:2][C@H:3]([N:25]1[C:33]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:32]2[C:27]([N:28]([CH3:43])[C:29](=[O:42])[N:30]([CH3:41])[C:31]2=[O:40])=[CH:26]1)[CH2:4][S:5][C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:54])=[O:53]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 86723513HCID 86723513, compound

Product 1

HCID 86723514HCID 86723514, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-6-(1-Hydroxy-3-(tritylthio)propan-2-yl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (step 2) (2.5 g, 4.25 mmol) was dissolved in DCM (80 mL) and triethylamine (1.186 mL, 8.51 mmol) was added followed by methanesulfonyl chloride (0.398 mL, 5.10 mmol). The mixture was stirred at room temperature for 2 hours, further methanesulfonyl chloride was added and the mixture stirred for 50 mins. The reaction mixture was quenched with sat. NaHCO3(aq) and extracted with DCM. The organic phase was passed through a hydrophobic frit and evaporated under vacuum. Purification by chromatography on silica, eluting with 20-100% EtOAc in iso-hexane gave the title compound.

Workup

  1. stirringthe mixture stirred for 50 mins
  2. customThe reaction mixture was quenched with sat. NaHCO3(aq)
  3. extractionextracted with DCM
  4. customevaporated under vacuum
  5. customPurification by chromatography on silica
  6. washeluting with 20-100% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-2ab462f002e240f9a4b7d0fa2b2bd74e
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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