Triethylamine → HCID 58504570, compound

HRID 2367523Notes

Reaction equation

HRID 2367523 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[Cl:13][C:14]1[N:19]=[C:18]([NH:20][CH3:21])[N:17]=[C:16]([N:22]2[C@H:27]([CH3:28])[CH2:26][O:25][C@H:24]([CH2:29][OH:30])[CH2:23]2)[CH:15]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:8][S:9]([O:30][CH2:29][C@H:24]1[O:25][CH2:26][C@@H:27]([CH3:28])[N:22]([C:16]2[CH:15]=[C:14]([Cl:13])[N:19]=[C:18]([NH:20][CH3:21])[N:17]=2)[CH2:23]1)(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 51353726HCID 51353726, compound

Product 1

HCID 58504570HCID 58504570, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (1.95 mL, 14.07 mmol) and methanesulfonyl chloride (0.52 mL, 6.67 mmol) were added dropwise to a solution of {(2S,5R)-4-[6-chloro-2-(methylamino)-4-pyrimidinyl]-5-methyl-2-morpholinyl}methanol (1.52 g, 5.57 mmol) in CH2Cl2 (50 mL) at 0° C., and the mixture was stirred at 0° C. under nitrogen for 45 minutes. It was then poured into saturated aqueous NaHCO3 (100 mL) and extracted with CH2Cl2 (3×100 mL). The extracts were dried (Na2SO4), filtered, and concentrated in vacuo to give the title compound (1.88 g) as a foam that was crushed into an off-white solid. LC-MS (ES) m/z=351, 353 [M+H]+.

Workup

  1. extractionextracted with CH2Cl2 (3×100 mL)
  2. dry with materialThe extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e1387d4bd8f24020922ccd1af37bdbce
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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