3-(Trifluoromethyl)phenylboronic acid → 2-chloromethyl-6-(3-trifluoromethyl-phenyl)-6H-imidazo[1,2-c]pyrimidin-5-one

HRID 538229Notes

Reaction equation

HRID 538229 reaction equation
N1C=CC(N)=NC1=O.[F:9][C:10]([F:21])([F:20])[C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.NC1C=CN(C2C=CC(F)=CC=2)C(=O)N=1.[Cl:37][CH2:38][C:39]1[N:40]=[C:41]2[CH:46]=[CH:45][N:44](C3C=CC(F)=CC=3)[C:43](=[O:54])[N:42]2[CH:55]=1>>[Cl:37][CH2:38][C:39]1[N:40]=[C:41]2[CH:46]=[CH:45][N:44]([C:13]3[CH:14]=[CH:15][CH:16]=[C:11]([C:10]([F:21])([F:20])[F:9])[CH:12]=3)[C:43](=[O:54])[N:42]2[CH:55]=1

Participants

5

Reactant 4

HCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 682901544-amino-1-(4-fluoro-phenyl)-1H-pyrimidin-2-oneHCID 682908442-chloromethyl-6-(4-fluoro-phenyl)-6H-imidazo[1,2-c]pyrimidin-5-oneHCID 178418229Cytosine

Product 1

HCID 682903742-chloromethyl-6-(3-trifluoromethyl-phenyl)-6H-imidazo[1,2-c]pyrimidin-5-one

Procedure

2-chloromethyl-6-(3-trifluoromethyl-phenyl)-6H-imidazo[1,2-c]pyrimidin-5-one was prepared from cytosine and 3-(trifluoromethyl)phenylboronic acid using the methods as described above for the preparation of 4-amino-1-(4-fluoro-phenyl)-1H-pyrimidin-2-one and 2-chloromethyl-6-(4-fluoro-phenyl)-6H-imidazo[1,2-c]pyrimidin-5-one.

Sources & evidence

ORD record
ord-42e02f5adf984af5a73d848853515935
Source dataset
uspto-grants-2014_10
Patent number
US08865725B2

Reaction notes

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