5-Pyrimidinecarboxamide, 4-amino-2-(ethylthio)-N-methoxy-N-methyl- → HCID 21070592, compound

HRID 1435378Notes

Reaction equation

HRID 1435378 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].[C:17]1([CH3:25])[CH:22]=[CH:21][C:20]([Mg]Br)=[CH:19][CH:18]=1>O1CCCC1>[NH2:15][C:7]1[C:6]([C:4]([C:20]2[CH:21]=[CH:22][C:17]([CH3:25])=[CH:18][CH:19]=2)=[O:5])=[CH:11][N:10]=[C:9]([S:12][CH2:13][CH3:14])[N:8]=1

Participants

4

Reactant 2

HCID 119748325-Pyrimidinecarboxamide, 4-amino-2-(ethylthio)-N-methoxy-N-methyl-HCID 178418370HCID 178418370, compound

Product 1

HCID 21070592HCID 21070592, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-amino-2-ethylsulfanyl-pyrimidine-5-carboxylic acid methoxy-methyl-amide (500 mg, 2.06 mmol, Example 1) in dry tetrahydrofuran (6 mL) at −30˜−40° C., was added 4-tolylmagnesium bromide (10.5 mL, Aldrich). The reaction was stirred at the same temperature for 2 hours before quenching with aqueous ammonium chloride. Work-up and purification as in Example 47 gave (4-amino-2-ethylsulfanyl-pyrimidin-5-yl)-p-tolyl-methanone as a white solid. MS (M+H)+, 274.

Workup

  1. custombefore quenching with aqueous ammonium chloride
  2. custompurification as in Example 47

Sources & evidence

ORD record
ord-66a0fec561604bc1b12d6adf15b9bef8
Source dataset
uspto-grants-2009_11
Patent number
US07615634B2

Reaction notes

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