Acetic Anhydride → 2-[6-ethyl-1-{[3-fluoro-2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl]-1-(4-methoxyphenyl)ethyl acetate

HRID 1889538Notes

Reaction equation

HRID 1889538 reaction equation
[CH2:1]([C:3]1[S:44][C:6]2[N:7]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[C:37]4[NH:41][C:40](=[O:42])[O:39][N:38]=4)=[CH:27][C:26]=3[F:43])[C:8](=[O:23])[N:9]([CH2:12][CH:13]([OH:22])[C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2].[C:45](OC(=O)C)(=[O:47])[CH3:46].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:45]([O:22][CH:13]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH2:12][N:9]1[C:10](=[O:11])[C:5]2[CH:4]=[C:3]([CH2:1][CH3:2])[S:44][C:6]=2[N:7]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[C:37]3[NH:41][C:40](=[O:42])[O:39][N:38]=3)=[CH:27][C:26]=2[F:43])[C:8]1=[O:23])(=[O:47])[CH3:46]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 1360523206-ethyl-1-{[3-fluoro-2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-3-[2-hydroxy-2-(4-methoxyphenyl)ethyl]thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 1360522772-[6-ethyl-1-{[3-fluoro-2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl]-1-(4-methoxyphenyl)ethyl acetateYield 71%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-ethyl-1-{[3-fluoro-2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-3-[2-hydroxy-2-(4-methoxyphenyl)ethyl]thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (0.3 g), acetic anhydride (0.07 mL), triethylamine (0.1 mL), N,N-dimethylpyridin-4-amine (0.006 g) and methylene chloride (20 mL) was stirred at room temperature for 16 hr. The reaction mixture was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration to give the title compound as colorless crystals (0.23 g, 71%).

Workup

  1. washThe reaction mixture was washed successively with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-8edc551c0d4242639d7fbc5f76917337
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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