(+)-5-Methoxycarbonyl-4-methoxymethyl-1,2,3,6-tetrahydro 2-oxo-6-(3,4-difluorophenyl)-1-[(4-nitrophenyloxy)carbonyl]pyrimidine → 4-(3,4-Difluorophenyl)-6-methoxymethyl-2-oxo-3-[3-(4-phenyl-4-(thiophen-2-yl)piperidin-1-yl)-propylcarbamoyl}-1,2,3,4-tetrahydropyrimidine-5-carboxylic Acid Methyl Ester

HRID 1066986Notes

Reaction equation

HRID 1066986 reaction equation
[N+](C1C=CC(O[C:11]([N:13]2[CH:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)[C:17]([C:27]([O:29][CH3:30])=[O:28])=[C:16]([CH2:31][O:32][CH3:33])[NH:15][C:14]2=[O:34])=[O:12])=CC=1)([O-])=O.[C:35]1([C:41]2([C:51]3[S:52][CH:53]=[CH:54][CH:55]=3)[CH2:46][CH2:45][N:44]([CH2:47][CH2:48][CH2:49][NH2:50])[CH2:43][CH2:42]2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)Cl>[CH3:30][O:29][C:27]([C:17]1[CH:18]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=2)[N:13]([C:11](=[O:12])[NH:50][CH2:49][CH2:48][CH2:47][N:44]2[CH2:43][CH2:42][C:41]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)([C:51]3[S:52][CH:53]=[CH:54][CH:55]=3)[CH2:46][CH2:45]2)[C:14](=[O:34])[NH:15][C:16]=1[CH2:31][O:32][CH3:33])=[O:28]

Participants

4

Reactant 2

HCID 10672264(+)-5-Methoxycarbonyl-4-methoxymethyl-1,2,3,6-tetrahydro 2-oxo-6-(3,4-difluorophenyl)-1-[(4-nitrophenyloxy)carbonyl]pyrimidineHCID 211963323-(4-Phenyl-4-thiophen-2-yl-piperidin-1-yl)propylamine

Product 1

HCID 206626554-(3,4-Difluorophenyl)-6-methoxymethyl-2-oxo-3-[3-(4-phenyl-4-(thiophen-2-yl)piperidin-1-yl)-propylcarbamoyl}-1,2,3,4-tetrahydropyrimidine-5-carboxylic Acid Methyl EsterYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 6-(3,4-difluorophenyl)-4-methoxymethyl-2-oxo-3,6-dihydro-2H-pyrimidine-1,5-dicarboxylic acid 5-methyl ester 1-(4-nitrophenyl)ester (29 mg, 0.06 mmol) in 2 ml of CH2Cl2 was added 3-(4-phenyl-4-thiophen-2-yl-piperidin-1-yl)propylamine (20 mg, 0.07 mmol) and the resulting solution was stirred for 2 h at 25° C. The reaction mixture was concentrated in vacuo to provide an oil which was subjected to column chromatography over silica gel (5% MeOH/CHCl3) to yield 25 mg (64%) of the desired product which was converted to a HCl salt and recrystallized from EtOAC-Et2O to afford 22 mg of the product as a white solid: mp 157-159° C.; Anal. Calc. For C33H36F2N4O5S requires C, 58.6; H, 5.33; N, 8.29. Found: C, 57.3; H, 5.45; 7.90.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto provide an oil which

Sources & evidence

ORD record
ord-0e2da3d8da7146c3932346a036a4eb56
Source dataset
uspto-grants-2001_06
Patent number
US06245773B1

Reaction notes

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