p-Toluenesulfonic acid monohydrate → 2-(1,3-benzoxazol-2-ylmethyl)-6-(morpholin-4-yl)pyrimidin-4(3H)-one
Reaction equation
O.CC1C=CC(S(O)(=O)=O)=CC=1.O[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21](=[O:36])[CH2:22][C:23]1[NH:24][C:25](=[O:35])[CH:26]=[C:27]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[N:28]=1>C1(C)C=CC=CC=1>[O:36]1[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:20]=[C:21]1[CH2:22][C:23]1[NH:24][C:25](=[O:35])[CH:26]=[C:27]([N:29]2[CH2:30][CH2:31][O:32][CH2:33][CH2:34]2)[N:28]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
20 mg of 4-methylbenzenesulphonic acid hydrate are added to a solution of 200 mg of N-(2-hydroxyphenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide in 40 ml of toluene. The reaction mixture is brought to reflux overnight. After cooling to 0° C., the insoluble material formed is filtered off. The filtrate is concentrated to dryness under reduced pressure and the residue is then chromatographed on a silica gel column, eluent: CH2Cl2/MeOH: 98/02 then 90/10. 16 mg of 2-(1,3-benzoxazol-2-ylmethyl)-6-(morpholin-4-yl)pyrimidin-4(3H)-one are thus obtained in the form of a white solid, the characteristics of which are the following:
Workup
- temperatureto reflux overnight
- customthe insoluble material formed
- filtrationis filtered off
- concentrationThe filtrate is concentrated to dryness under reduced pressure
- customthe residue is then chromatographed on a silica gel column, eluent
Sources & evidence
- ORD record
- ord-395068a204e14b9bb8686ce22d11db7b
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507483B2
Reaction notes
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