1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-(3,4-Dimethoxyphenyl)-N-{4-[(1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidin-6-yl)methyl]phenyl}-butanamide

HRID 567928Notes

Reaction equation

HRID 567928 reaction equation
C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH2:32][CH2:33][CH2:34][C:35]([OH:37])=O)[CH:27]=[CH:28][C:29]=1[O:30][CH3:31].[NH2:38][C:39]1[CH:44]=[CH:43][C:42]([CH2:45][C:46]2[S:61][C:49]3[N:50]([CH2:57][CH:58]([CH3:60])[CH3:59])[C:51](=[O:56])[N:52]([CH3:55])[C:53](=[O:54])[C:48]=3[CH:47]=2)=[CH:41][CH:40]=1>ClCCl>[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH2:32][CH2:33][CH2:34][C:35]([NH:38][C:39]2[CH:44]=[CH:43][C:42]([CH2:45][C:46]3[S:61][C:49]4[N:50]([CH2:57][CH:58]([CH3:59])[CH3:60])[C:51](=[O:56])[N:52]([CH3:55])[C:53](=[O:54])[C:48]=4[CH:47]=3)=[CH:41][CH:40]=2)=[O:37])[CH:27]=[CH:28][C:29]=1[O:30][CH3:31]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 3236754-(3,4-Dimethoxyphenyl)butanoic acidHCID 222580286-(4-Aminophenylmethyl)-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 222580544-(3,4-Dimethoxyphenyl)-N-{4-[(1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidin-6-yl)methyl]phenyl}-butanamideYield 26.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-ethyl-N′-[3-(dimethylamino)propyl]carbodiimide (37 mg), 1-hydroxybenzotriazole (26 mg) and 4-(3,4-dimethyloxyphenyl)butanoic acid (36 mg) in dichloromethane (6 ml) was added 6-(4-aminophenylmethyl)-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-(1H, 3H)-dione (45 mg) in dichloromethane (2 ml). The reaction mixture was stirred overnight and then washed with half saturated sodium hydrogen carbonate and extracted into ethyl acetate. The organic layer was dried over magnesium sulfate, evaporated and the residue was purified by normal phase HPLC (isohexane:ethyl acetate 50-0:50-100) to give the title compound (19 mg) as a foam.

Workup

  1. washwashed with half saturated sodium hydrogen carbonate
  2. extractionextracted into ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated
  5. customthe residue was purified by normal phase HPLC (isohexane:ethyl acetate 50-0:50-100)

Sources & evidence

ORD record
ord-bcfbf8fc4e564feea9c8c499596259d4
Source dataset
uspto-grants-2001_01
Patent number
US06180635B2

Reaction notes

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