Water → (R)-2-{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidin-4-ylamino}-3-methyl-butyramide

HRID 70087

Reaction equation

HRID 70087 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:11][C@H:12]([CH:16]([CH3:18])[CH3:17])[C:13]([NH2:15])=[O:14])[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C.O>O1CCOCC1>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]2[CH2:31][CH2:30][N:29]([C:2]3[N:3]=[C:4]([NH:11][C@H:12]([CH:16]([CH3:18])[CH3:17])[C:13]([NH2:15])=[O:14])[C:5]4[S:10][CH2:9][CH2:8][C:6]=4[N:7]=3)[CH2:28][CH2:27]2)=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 974781-(4-Chlorophenyl)piperazineHCID 59708380(R)-2-(2-chloro-6,7-dihydro-thieno[3,2-d]pyrimidin-4-ylamino)-3-methyl-butyramide

Product 1

HCID 59708455(R)-2-{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidin-4-ylamino}-3-methyl-butyramideYield 88.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

400 mg (R)-2-(2-chloro-6,7-dihydro-thieno[3,2-d]pyrimidin-4-ylamino)-3-methyl-butyramide, 750 mg 1-(4-chloro-phenyl)-piperazine and 1.2 ml diisopropylethylamine are placed in 9 ml dioxane, then heated in the microwave for 1 hour and 45 minutes at 160° C. Then water is added. The precipitate formed is suction filtered and dried. 550 mg of the product are obtained as a powder. Analytical HPLC (method B): RT=3.03 min.

Workup

  1. customThe precipitate formed
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-f1f6c059d996401f91be22d95e1c3696
Source dataset
uspto-grants-2014_09
Patent number
US08822474B2

Linked notes

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