3-Methoxybenzaldehyde → 5-Methyl-2-methylthio-N-[2-amino-1-{3-methoxyphenyl}-2-oxoethyl]-N-(4-methylbenzyl)pyrimidine-4-carboxamide

HRID 895287Notes

Reaction equation

Cl[C:2]1[C:3]([C:10]([N:12]([CH:21]([C:25]2[CH:34]=[CH:33][C:28]3OC[CH2:31][O:32][C:27]=3[CH:26]=2)[C:22]([NH2:24])=[O:23])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)=[O:11])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[CH3:35]C1C(C(O)=S)=NC(C)=NC=1.COC1C=C(C=CC=1)C=O>>[CH3:35][C:2]1[C:3]([C:10]([N:12]([CH:21]([C:25]2[CH:34]=[CH:33][CH:28]=[C:27]([O:32][CH3:31])[CH:26]=2)[C:22]([NH2:24])=[O:23])[CH2:13][C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)=[O:11])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1

Participants

Reactant 3

HCID 115693-Methoxybenzaldehyde

HCID 100061165-Chloro-2-methylthio-N-[2-amino-1-{1,4-benzodioxan-6-yl}-2-oxoethyl]-N-(4-methylbenzyl)pyrimidine-4-carboxamide

HCID 178432746HCID 178432746, compound

Product 1

HCID 223862065-Methyl-2-methylthio-N-[2-amino-1-{3-methoxyphenyl}-2-oxoethyl]-N-(4-methylbenzyl)pyrimidine-4-carboxamide

Procedure

This was prepared in the same manner as the product from example 242 using 5-methyl-2-methylthiopyrimidine-4-carboxylic acid (preparation 17) and 3-methoxybenzaldehyde as the acid and aldehyde components to give the title compound as a solid, 0.97 g, (72%).

Sources & evidence

ORD record: ord-d0e7ce75b7024ca0a12c8dc4683f2756
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06914160B1

Reaction notes

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