Triethylamine → HCID 58504487, compound

HRID 2367321Notes

Reaction equation

HRID 2367321 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[NH2:13][C:14]1[N:19]=[C:18]([N:20]2[C@H:25]([CH3:26])[CH2:24][O:23][C@H:22]([CH2:27][OH:28])[CH2:21]2)[CH:17]=[C:16]([Cl:29])[N:15]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:8][S:9]([O:28][CH2:27][C@H:22]1[O:23][CH2:24][C@@H:25]([CH3:26])[N:20]([C:18]2[CH:17]=[C:16]([Cl:29])[N:15]=[C:14]([NH2:13])[N:19]=2)[CH2:21]1)(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 516892Sodium BicarbonateHCID 51353725HCID 51353725, compound

Product 1

HCID 58504487HCID 58504487, compoundYield 117.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.65 mL, 4.69 mmol) and methanesulfonyl chloride (0.34 mL, 4.36 mmol) were added dropwise to a solution of [(2S,5R)-4-(2-amino-6-chloro-4-pyrimidinyl)-5-methyl-2-morpholinyl]methanol (1.00 g, 3.88 mmol) in CH2Cl2 (35 mL), and the mixture was stirred at room temperature under nitrogen. After 75 minutes another portion each of triethylamine (0.16 mL, 1.16 mmol) and methanesulfonyl chloride (0.076 mL, 0.97 mmol) were added dropwise and stirring continued for an additional 30 minutes. The reaction mixture was then poured into saturated aqueous NaHCO3 (100 mL) and extracted with CH2Cl2 (3×75 mL). The extracts were dried (Na2SO4), filtered, and concentrated in vacuo to give the title compound (1.53 g, about 85% purity) as a white foam. LC-MS (ES) m/z=337, 339 [M+H]+.

Workup

  1. stirringstirring
  2. extractionextracted with CH2Cl2 (3×75 mL)
  3. dry with materialThe extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b9e79670ed794ce3a14c4bb4008cedfd
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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