Water → HCID 86590465, compound

HRID 1352736Notes

Reaction equation

HRID 1352736 reaction equation
N1C=CC=CC=1CO[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]([Cl:25])[CH:18]=2)[C:12](C(O)=O)=[CH:11][N:10]=1.[OH:29][CH2:30]C1N=CC=CN=1.C[N:38]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=1)C.[OH2:46]>CN(C)C=O>[N:41]1[CH:42]=[CH:43][CH:44]=[N:38][C:40]=1[CH2:45][O:46][C:30]([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]([Cl:25])[CH:18]=2)[CH:12]=[CH:11][N:10]=1)=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 218852-DimethylaminopyridineHCID 27630242-PyrimidinemethanolHCID 17848330HCID 17848330, compound

Product 1

HCID 86590465HCID 86590465, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(2-pyridylmethoxy)-5-carboxy-4-(3-chloro-4-methoxybenzylamino)pyrimidine (prepared in Example 68-(3)) 100 mg, 2-hydroxymethylpyrimidine 30 mg, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimido hydrochloride 53 mg and dimethylaminopyridine 33 mg in dimethylformamide 3 ml is stirred at room temperature for 2 hours. The reaction mixture is poured into water and extracted with ethyl acetate. The organic layer is washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue is purified with preparative thin-layer chromatography (solvent; chloroform:methanol=25:1) and triturated with diethyl ether to give 2-(2-pyridylmethoxy)-5-(2-pyrimidinylmethoxycarbonyl-4-(3-chloro-4-methoxybenzylamino) pyrimidine 60 mg. mp 137–139° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified with preparative thin-layer chromatography (solvent; chloroform:methanol=25:1)
  6. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-a5b29a158968487a83cc4bf6ab6b0bc2
Source dataset
uspto-grants-2007_05
Patent number
US07220736B2

Reaction notes

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