Triethylamine → HCID 17848315, compound

HRID 917585Notes

Reaction equation

HRID 917585 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:9]1[N:14]=[C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([NH:25][CH3:26])[CH:18]=2)[C:12]([C:27]([C:29]2[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=2)=[O:28])=[CH:11][N:10]=1.[S:41](Cl)([CH3:44])(=[O:43])=[O:42].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(Cl)Cl.C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:9]1[N:14]=[C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([N:25]([S:41]([CH3:44])(=[O:43])=[O:42])[CH3:26])[CH:18]=2)[C:12]([C:27]([C:29]2[CH:30]=[C:31]([O:39][CH3:40])[C:32]([O:37][CH3:38])=[C:33]([O:35][CH3:36])[CH:34]=2)=[O:28])=[CH:11][N:10]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 10302584HCID 10302584, compound

Product 1

HCID 17848315HCID 17848315, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(2-pyridylmethoxy)-5-(3,4,5-trimethoxyphenyl-carbonyl)-4-(3-metylamino-4-methoxybenzylamino)pyrimidine (prepared in Example 48) 42 mg in methylene chloride 3 ml are added mesyl chloride 48 mg and triethylamine 69 mg, for three times at one hour intervals. The reaction mixture is stirred for 1 hour at room temperature. Ethyl acetate and an aqueous saturated sodium hydrogen carbonate solution is added thereto. The organic layer is separated, washed with brine and dried over anhydrous sodium sulfate. After filtration of sodium sulfate the filtrate is concentrated in vacuo and the residue is purified by preparative thin-layer chromatograph (2 plates, solvent:ethyl acetate) to give 2-(2-pyridylmethoxy)-5-(3,4,5-trimethoxyphenylcarbonyl)-4-[4-methoxy-3-(N-methylmethansulfonylamino)benzylamino]pyrimidine as a colorless amorphous 20 mg.

Workup

  1. customThe organic layer is separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration of sodium sulfate the filtrate
  5. concentrationis concentrated in vacuo
  6. customthe residue is purified by preparative thin-layer chromatograph (2 plates, solvent:ethyl acetate)

Sources & evidence

ORD record
ord-69701b7e3f304a8990dffd49612d4fa2
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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