Dichloromethane → HCID 136041774, compound

HRID 1890476Notes

Reaction equation

HRID 1890476 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH:9][C:10](=O)[CH2:11][C:12]2[NH:13][C:14](=[O:24])[CH:15]=[C:16]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:17]=2)=[C:4]([OH:26])[CH:3]=1.O.CC1C=CC(S(O)(=O)=O)=CC=1.C(Cl)Cl.C(Cl)Cl.CO>C1(C)C(C)=CC=CC=1.C(OCC)C>[F:8][C:7]1[C:2]([F:1])=[CH:3][C:4]2[O:26][C:10]([CH2:11][C:12]3[NH:13][C:14](=[O:24])[CH:15]=[C:16]([N:18]4[CH2:19][CH2:20][O:21][CH2:22][CH2:23]4)[N:17]=3)=[N:9][C:5]=2[CH:6]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 21226129Dichloromethane methanolHCID 136355297N-(4,5-difluoro-2-hydroxyphenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide

Product 1

HCID 136041774HCID 136041774, compoundYield 14.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7237O-XyleneSolvent

Procedure

The product can be prepared as described in stage 2 of Example 12, but using 465 mg of N-(4,5-difluoro-2-hydroxyphenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide in 30 ml of xylene and 77 mg of 4-methylbenzenesulphonique acid hydrate. After refluxing for six hours, addition of 100 mg of 4-methylbenzenesulphonic acid hydrate and purification by silica column chromatography, eluent: gradient of pure CH2Cl2 to CH2Cl2/MeOH: 96/04, the product obtained is taken up with 20 ml of diethyl ether and then spin-filter-dried and dried under vacuum. 63 mg of 2-[(5,6-difluoro-1,3-benzoxazol-2-yl)methyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one are obtained in the form of a white solid, the characteristics of which are the following:

Workup

  1. customThe product can be prepared
  2. temperatureAfter refluxing for six hours
  3. customspin-filter-dried
  4. customdried under vacuum

Sources & evidence

ORD record
ord-16d701afb5aa496cba2bc09ced99bced
Source dataset
uspto-grants-2013_08
Patent number
US08507483B2

Reaction notes

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