Water → ethyl 4-{4-[4-(3-chloro-phenylamino)-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-2-yl]-piperazin-1-yl}-benzoate

HRID 70112Notes

Reaction equation

HRID 70112 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[C:5]2[S:10](=[O:11])[CH2:9][CH2:8][C:6]=2[N:7]=1.[N:20]1([C:26]2[CH:36]=[CH:35][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][CH:27]=2)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(N(C(C)C)CC)(C)C.O>O1CCOCC1>[Cl:19][C:15]1[CH:14]=[C:13]([NH:12][C:4]2[C:5]3[S:10](=[O:11])[CH2:9][CH2:8][C:6]=3[N:7]=[C:2]([N:23]3[CH2:22][CH2:21][N:20]([C:26]4[CH:27]=[CH:28][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:35][CH:36]=4)[CH2:25][CH2:24]3)[N:3]=2)[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 2761178Ethyl 4-(piperazin-1-yl)benzoateHCID 59708482(2-chloro-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-4-yl)-(3-chloro-phenyl)-amine

Product 1

HCID 59708453ethyl 4-{4-[4-(3-chloro-phenylamino)-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-2-yl]-piperazin-1-yl}-benzoateYield 77.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

5.44 g (2-chloro-5-oxo-6,7-dihydro-5H-5λ4-thieno[3,2-d]pyrimidin-4-yl)-(3-chloro-phenyl)-amine (prepared from 2,4-dichloro-6,7-dihydro-thieno[3,2-d]pyrimidine and 3-chloroaniline as described in Example 28, see scheme 2), 8.00 g ethyl 4-piperazin-1-yl-benzoate and 4.80 ml diisopropylethylamine are placed in 54 ml dioxane, then heated to 160° C. in the microwave for 0.7 hours. Then the reaction mixture is cooled and mixed with water. The precipitate formed is suction filtered and stirred with petroleum ether/ethyl acetate 1:1, suction filtered and dried. 6.90 g of the product are obtained as a powder.

Workup

  1. temperatureThen the reaction mixture is cooled
  2. customThe precipitate formed
  3. filtrationfiltered
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-94ff7294f917406789c86a1d7cd85564
Source dataset
uspto-grants-2014_09
Patent number
US08822474B2

Reaction notes

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