3-hydroxy-N,N-dimethylbenzamide → 2-(3-Dimethylaminocarbonylphenoxy)-4-(ethoxycarbonylmethyl)amino-5-nitro-6-(2-benzyloxy-5-cyanophenoxy)pyrimidine

HRID 1456942Notes

Reaction equation

HRID 1456942 reaction equation
CS([C:5]1[N:10]=[C:9]([NH:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([N+:18]([O-:20])=[O:19])=[C:7]([O:21][C:22]2[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[CH:24][C:23]=2[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:6]=1)(=O)=O.[CH3:38][N:39]([CH3:49])[C:40]([C:42]1[CH:43]=[C:44]([OH:48])[CH:45]=[CH:46][CH:47]=1)=[O:41]>>[CH3:38][N:39]([CH3:49])[C:40]([C:42]1[CH:43]=[C:44]([CH:45]=[CH:46][CH:47]=1)[O:48][C:5]1[N:10]=[C:9]([NH:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([N+:18]([O-:20])=[O:19])=[C:7]([O:21][C:22]2[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[CH:24][C:23]=2[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:6]=1)=[O:41]

Participants

3

Reactant 2

HCID 6375243-hydroxy-N,N-dimethylbenzamideHCID 221025672-Methylsulfonyl-4-(ethoxycarbonylmethyl)amino-5-nitro-6-(2-benzyloxy-5-cyanophenoxy)pyrimidine

Product 1

HCID 221029812-(3-Dimethylaminocarbonylphenoxy)-4-(ethoxycarbonylmethyl)amino-5-nitro-6-(2-benzyloxy-5-cyanophenoxy)pyrimidine

Procedure

In a similar manner, 2-methylsulfonyl-4-(ethoxycarbonylmethyl)amino-5-nitro-6-(2-benzyloxy-5-cyanophenoxy)pyrimidine, a compound of formula (M), prepared as described below in Preparation 4, is treated with 3-(dimethylaminocarbonyl)phenol, a compound of formula (B) to afford 2-(3-dimethylaminocarbonylphenoxy)-4-(ethoxycarbonylmethyl)amino-5-nitro-6-(2-benzyloxy-5-cyanophenoxy)pyrimidine, a compound of formula (N).

Workup

  1. customas described below in Preparation 4

Sources & evidence

ORD record
ord-717e34d9ca5d43168b5b93e0b4558d14
Source dataset
uspto-grants-1998_12
Patent number
US05846970

Reaction notes

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