1-Fluoro-2-iodobenzene → (4-Amino-2-ethylsulfanyl-pyrimidin-5-yl)-(2-fluoro-phenyl)-methanone

HRID 1371612Notes

Reaction equation

HRID 1371612 reaction equation
CON(C)[C:4]([C:6]1[C:7]([NH2:15])=[N:8][C:9]([S:12][CH2:13][CH3:14])=[N:10][CH:11]=1)=[O:5].[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Li].FC1C=CC=CC=1I>>[NH2:15][C:7]1[C:6]([C:4]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[F:17])=[O:5])=[CH:11][N:10]=[C:9]([S:12][CH2:13][CH3:14])[N:8]=1

Participants

4

Reactant 3

HCID 676731-Fluoro-2-iodobenzeneHCID 119748325-Pyrimidinecarboxamide, 4-amino-2-(ethylthio)-N-methoxy-N-methyl-HCID 178506686HCID 178506686, compound

Product 1

HCID 11975323(4-Amino-2-ethylsulfanyl-pyrimidin-5-yl)-(2-fluoro-phenyl)-methanone

Procedure

The same procedure was used as described in Example 2, starting from 4-amino-2-ethylsulfanyl-pyrimidine-5-carboxylic acid methoxy-methylamide (from Example 1) and a solution of 2-fluorophenyllithium (˜3 equiv, freshly prepared from 1-fluoro-2-iodobenzene as in Example 2A), to give (4-amino-2-ethylsulfanyl-pyrimidin-5-yl)-(2-fluoro-phenyl)-methanone. MS (M+H)+: 278.

Sources & evidence

ORD record
ord-79efe14ffa2248eca87bf8f0845c7f96
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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