p-Toluenesulfonic acid monohydrate → 2-[(5-fluoro-1,3-benzoxazol-2-yl)methyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one

HRID 1890464Notes

Reaction equation

HRID 1890464 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([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)[CH:7]=1.O.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:25][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)=[N:8][C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 136332411N-(5-fluoro-2-hydroxyphenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide

Product 1

HCID 1360417532-[(5-fluoro-1,3-benzoxazol-2-yl)methyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The product is prepared according to the procedure described in Stage 2 of Example 2, using 700 mg of N-(5-fluoro-2-hydroxyphenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide and 292 mg of 4-methylbenzenesulphonic acid hydrate, and replacing the toluene with xylene. After purification by silica gel column chromatography, elution being carried out with a mixture of CH2Cl2/MeOH: 98/02, then CH2Cl2/MeOH: 95/05, followed by recrystallization from methanol, 188 mg of 2-[(5-fluoro-1,3-benzoxazol-2-yl)methyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one are obtained in the form of a brown solid, the characteristics of which are the following:

Workup

  1. customThe product is prepared
  2. customAfter purification
  3. washby silica gel column chromatography, elution
  4. additionbeing carried out with a mixture of CH2Cl2/MeOH
  5. custom98/02, then CH2Cl2/MeOH: 95/05, followed by recrystallization from methanol, 188 mg of 2-[(5-fluoro-1,3-benzoxazol-2-yl)methyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one
  6. customare obtained in the form of a brown solid

Sources & evidence

ORD record
ord-9554a5667e32464fbc4b37d77cf34296
Source dataset
uspto-grants-2013_08
Patent number
US08507483B2

Reaction notes

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