2-Iodotoluene → (4-Amino-2-ethylsulfanyl-pyrimidin-5-yl)-o-tolyl-methanone

HRID 1371611Notes

Reaction equation

HRID 1371611 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([CH3:24])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Li].IC1C=CC=CC=1C>>[NH2:15][C:7]1[C:6]([C:4]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH3:24])=[O:5])=[CH:11][N:10]=[C:9]([S:12][CH2:13][CH3:14])[N:8]=1

Participants

4

Reactant 3

HCID 51282-IodotolueneHCID 119748325-Pyrimidinecarboxamide, 4-amino-2-(ethylthio)-N-methoxy-N-methyl-HCID 178506678C7H7Li

Product 1

HCID 11975322(4-Amino-2-ethylsulfanyl-pyrimidin-5-yl)-o-tolyl-methanone

Procedure

The same procedure was used as described in Example 2, starting from 4-amino-2-ethylsulfanyl-pyrimidine-5-carboxylic acid methoxy-methyl-amide (from Example 1) and a solution of 2-tolyllithium (−3 equiv, freshly prepared from 2-iodotoluene, as in Example 2A), to give (4-amino-2-ethylsulfanyl-pyrimidin-5-yl)-o-tolyl-methanone as a white solid. MS (M+H)+: 274.

Sources & evidence

ORD record
ord-6575860e3ba847c180ba9430e1482f3e
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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