p-Toluenesulfonic acid monohydrate → HCID 136041779, compound

HRID 1890480Notes

Reaction equation

HRID 1890480 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)[CH2:10][C:11]2[NH:12][C:13](=[O:23])[CH:14]=[C:15]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[N:16]=2)=[C:4]([OH:25])[CH:3]=1.[OH2:26].[CH3:27]C1C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[CH3:27][O:26][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:9]([CH2:10][C:11]3[NH:12][C:13](=[O:23])[CH:14]=[C:15]([N:17]4[CH2:18][CH2:19][O:20][CH2:21][CH2:22]4)[N:16]=3)[O:25][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 136332410N-(4-fluoro-2-hydroxyphenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydro-pyrimidin-2-yl]acetamide

Product 1

HCID 136041779HCID 136041779, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
20 °C

Procedure

500 mg of the N-(4-fluoro-2-hydroxyphenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide are mixed into 40 ml of xylene, and 155 mg of 4-methylbenzenesulphonic acid hydrate are added. The reaction mixture is brought to reflux for 3 hours. After cooling to 20° C., the reaction mixture is concentrated to dryness under reduced pressure and then the residue is chromatographed on a silica gel column, eluent: CH2Cl2/MeOH: 95/05. 220 mg of 2-[(6-methoxy-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. additionare added
  2. temperatureto reflux for 3 hours
  3. concentrationthe reaction mixture is concentrated to dryness under reduced pressure
  4. customthe residue is chromatographed on a silica gel column, eluent

Sources & evidence

ORD record
ord-2940b2da06e64df0aa55737e1e439367
Source dataset
uspto-grants-2013_08
Patent number
US08507483B2

Reaction notes

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