3-Chloroaniline → (3-Chlorophenyl)-[2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl]amine

HRID 1788009Notes

Reaction equation

HRID 1788009 reaction equation
Cl[C:2]1[C:3]2[S:22][CH2:21][CH2:20][C:4]=2[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[N:7]=1.[Cl:23][C:24]1[CH:25]=[C:26]([NH2:30])[CH:27]=[CH:28][CH:29]=1.C(N(C(C)C)CC)(C)C>C(OCC)(=O)C>[Cl:23][C:24]1[CH:25]=[C:26]([NH:30][C:2]2[C:3]3[S:22][CH2:21][CH2:20][C:4]=3[N:5]=[C:6]([N:8]3[CH2:9][CH2:10][N:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:12][CH2:13]3)[N:7]=2)[CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 79323-ChloroanilineHCID 81531DiisopropylethylamineHCID 866162644-Chloro-2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidine

Product 1

HCID 11948305(3-Chlorophenyl)-[2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl]amine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.320 g (0.96 mmol) of 4-chloro-2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidine (V), 1.0 mL (9.5 mmol) of 3-chlorophenylamine, and 0.33 mL (1.92 mmol) of diisopropylethylamine are combined and the mixture is reacted for 0.5 hours at 130° C. in the microwave. Then the reaction mixture is combined with ethyl acetate and acidically extracted. The organic phase is dried and evaporated to dryness. The residue is combined with acetonitrile, water, and trifluoroacetic acid. The phase containing the product I is purified by chromatography through an RP column by HPLC (column: Microsorb, RP-C18, 300 Å, 10 μm, 21.4*250 mm, eluant: acetonitrile+0.1% formic acid (A), water+0.13% formic acid (B)).

Workup

  1. customthe mixture is reacted for 0.5 hours at 130° C. in the microwave
  2. extractionacidically extracted
  3. customThe organic phase is dried
  4. customevaporated to dryness
  5. additionThe phase containing the product I
  6. customis purified by chromatography through an RP column by HPLC (column: Microsorb, RP-C18, 300 Å, 10 μm, 21.4*250 mm, eluant: acetonitrile+0.1% formic acid (A), water+0.13% formic acid (B))

Sources & evidence

ORD record
ord-5b181300b2b640b3beb4612b51da751a
Source dataset
uspto-grants-2009_03
Patent number
US07511045B2

Reaction notes

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