5-Pyrimidinecarboxamide, 4-amino-2-(ethylthio)-N-methoxy-N-methyl- → (4-Amino-2-ethylsulfanyl-pyrimidin-5-yl)-(4-chloro-5-fluoro-2-methoxy-phenyl)-methanone

HRID 1371813Notes

Reaction equation

HRID 1371813 reaction equation
[Cl:1][C:2]1[C:3]([F:11])=[CH:4][C:5](I)=[C:6]([O:8][CH3:9])[CH:7]=1.C([Mg]Cl)(C)C.CON(C)[C:20]([C:22]1[C:23]([NH2:31])=[N:24][C:25]([S:28][CH2:29][CH3:30])=[N:26][CH:27]=1)=[O:21]>O1CCCC1>[NH2:31][C:23]1[C:22]([C:20]([C:5]2[CH:4]=[C:3]([F:11])[C:2]([Cl:1])=[CH:7][C:6]=2[O:8][CH3:9])=[O:21])=[CH:27][N:26]=[C:25]([S:28][CH2:29][CH3:30])[N:24]=1

Participants

5

Reactant 3

HCID 119748325-Pyrimidinecarboxamide, 4-amino-2-(ethylthio)-N-methoxy-N-methyl-HCID 210706301-Chloro-2-fluoro-4-iodo-5-methoxybenzeneHCID 178418918HCID 178418918, compound

Product 1

HCID 21070583(4-Amino-2-ethylsulfanyl-pyrimidin-5-yl)-(4-chloro-5-fluoro-2-methoxy-phenyl)-methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-chloro-4-fluoro-2-iodoanisole (1.0 g, Example 375) was added isopropylmagnesium chloride (1.92 mL, 2M in tetrahydrofuran, Aldrich) and the reaction was stirred at −40 to −35° C. for 40 minutes before 4-amino-2-ethylsulfanyl-pyrimidine-5-carboxylic acid methoxy-methyl-amide (170 mg, Example 1) in tetrahydrofuran (4 mL) was added. The resulting reaction was quenched with aqueous ammonium chloride. Work-up and purification as in Example 47 gave (4-amino-2-ethylsulfanyl-pyrimidin-5-yl)-(4-chloro-5-fluoro-2-methoxy-phenyl)-methanone. MS (M+H)+, 342.

Workup

  1. additionwas added
  2. customThe resulting reaction
  3. customwas quenched with aqueous ammonium chloride
  4. custompurification as in Example 47

Sources & evidence

ORD record
ord-4fedf446e041462a8f56b95999ffa056
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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