Diethyl Ether → 2-[(7-fluoro-1,3-benzoxazol-2-yl)methyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one

HRID 1890470Notes

Reaction equation

HRID 1890470 reaction equation
O.CC1C=CC(S(O)(=O)=O)=CC=1.[F:13][C:14]1[C:15]([OH:37])=[C:16]([NH:20][C:21](=O)[CH2:22][C:23]2[NH:24][C:25](=[O:35])[CH:26]=[C:27]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[N:28]=2)[CH:17]=[CH:18][CH:19]=1.C(OCC)C>C1(C)C(C)=CC=CC=1>[F:13][C:14]1[C:15]2[O:37][C:21]([CH2:22][C:23]3[NH:24][C:25](=[O:35])[CH:26]=[C:27]([N:29]4[CH2:30][CH2:31][O:32][CH2:33][CH2:34]4)[N:28]=3)=[N:20][C:16]=2[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 521998p-Toluenesulfonic acid monohydrateHCID 136041791N-(3-fluoro-2-hydroxyphenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide

Product 1

HCID 1360417642-[(7-fluoro-1,3-benzoxazol-2-yl)methyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-oneYield 38.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

42 mg of 4-methylbenzenesulphonic acid hydrate are added to a solution of 300 mg of N-(3-fluoro-2-hydroxyphenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide in 20 ml of xylene. After refluxing for six hours (assembly with Dean-Stark apparatus), the medium is concentrated to dryness under reduced pressure. After purification by silica column chromatography of the solid residue, eluent: gradient of pure CH2Cl2 to CH2Cl2/MeOH: 95/05, the product obtained is taken up with twice 20 ml of diethyl ether and then spin-filter-dried and dried under vacuum. 110 mg of 2-[(7-fluoro-1,3-benzoxazol-2-yl)methyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one are obtained in the form of a white powder, the characteristics of which are the following:

Workup

  1. temperatureAfter refluxing for six hours (assembly with Dean-Stark apparatus), the medium
  2. concentrationis concentrated to dryness under reduced pressure
  3. customAfter purification by silica column chromatography of the solid residue, eluent
  4. customgradient of pure CH2Cl2 to CH2Cl2/MeOH: 95/05, the product obtained
  5. customspin-filter-dried
  6. customdried under vacuum

Sources & evidence

ORD record
ord-b87e563c53814518b32d6b0ebba30ae5
Source dataset
uspto-grants-2013_08
Patent number
US08507483B2

Reaction notes

Loading…