p-Toluenesulfonic acid monohydrate → HCID 136041763, compound

HRID 1890467Notes

Reaction equation

HRID 1890467 reaction equation
[Br:1][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.O.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[Br:1][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 136355296HCID 136355296, compound

Product 1

HCID 136041763HCID 136041763, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The product is prepared according to the procedure described in Example 2, using 316 mg of N-(4-bromo-2-hydroxyphenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide and 73 mg of 4-methylbenzenesulphonic acid hydrate, and replacing the toluene with xylene. After recrystallization from 30 ml of ethanol, 5 ml of methanol and 5 ml of dichloromethane and then purification of the formed precipitate by silica column chromatography, eluent: CH2Cl2/MeOH: 90/10, 70 mg of 2-[(6-bromo-1,3-benzoxazol-2-yl)methyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one are obtained in the form of an off-white solid, the characteristics of which are the following:

Workup

  1. customThe product is prepared
  2. customAfter recrystallization from 30 ml of ethanol, 5 ml of methanol and 5 ml of dichloromethane
  3. custompurification of the formed precipitate by silica column chromatography, eluent

Sources & evidence

ORD record
ord-80c229757c3b49b9b03fa1cfbd192565
Source dataset
uspto-grants-2013_08
Patent number
US08507483B2

Reaction notes

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