p-Toluenesulfonic acid monohydrate → HCID 136041810, compound

HRID 1890486Notes

Reaction equation

HRID 1890486 reaction equation
O.CC1C=CC(S(O)(=O)=O)=CC=1.[OH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16](O)[C:15]=1[NH:21][C:22](=[O:37])[CH2:23][C:24]1[NH:25][C:26](=[O:36])[CH:27]=[C:28]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[N:29]=1>C1(C)C(C)=CC=CC=1>[OH:13][C:14]1[C:15]2[N:21]=[C:22]([CH2:23][C:24]3[NH:25][C:26](=[O:36])[CH:27]=[C:28]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[N:29]=3)[O:37][C:16]=2[CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 136355298HCID 136355298, compound

Product 1

HCID 136041810HCID 136041810, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
0 °C

Procedure

239 mg of 4-methylbenzenesulphonic acid hydrate are added to a solution of 870 mg of N-(2,6-dihydroxyphenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide in 60 ml of ortho-xylene. The reaction mixture is brought to reflux for 4 hours. After cooling to 0° C., the insoluble material formed is filtered off. The filtrate is concentrated to dryness under reduced pressure and then the residue is chromatographed on a silica gel column, elution being carried out with 90/10 CH2Cl2/MeOH. 654 mg of 2-[(4-hydroxy-1,3-benzoxazol-2-yl)methyl]-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

  1. temperatureto reflux for 4 hours
  2. customthe insoluble material formed
  3. filtrationis filtered off
  4. concentrationThe filtrate is concentrated to dryness under reduced pressure
  5. customthe residue is chromatographed on a silica gel column, elution

Sources & evidence

ORD record
ord-d4caf0c4406f4cddb4b5003b64ba1e6c
Source dataset
uspto-grants-2013_08
Patent number
US08507483B2

Reaction notes

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