Ammonia → {2-[4-(4-chloro-phenyl)-piperazin-1-yl]-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-4-yl}-(3-morpholin-ylmethyl-phenyl)-amine

HRID 70085Notes

Reaction equation

HRID 70085 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[N:15]=[C:16]([NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][N:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)[CH:25]=4)[C:17]4[S:22][CH2:21][CH2:20][C:18]=4[N:19]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH:37]O.N>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:14]3[N:15]=[C:16]([NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][N:31]5[CH2:32][CH2:33][O:34][CH2:35][CH2:36]5)[CH:25]=4)[C:17]4[S:22](=[O:37])[CH2:21][CH2:20][C:18]=4[N:19]=3)[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 784Hydrogen PeroxideHCID 59708439{2-[4-(4-Chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidin-4-yl}-(3-morpholin-4-ylmethyl-phenyl)-amine

Product 1

HCID 59708388{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-4-yl}-(3-morpholin-ylmethyl-phenyl)-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
10 °C

Procedure

313.80 mg {2-[4-(4-chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidin-4-yl}-(3-morpholin-4-ylmethyl-phenyl)-amine are placed in 2.70 ml glacial acetic acid and cooled to 10° C. 57 μl hydrogen peroxide (35%) are added dropwise, then the mixture is stirred for 0.25 hours. Then the reaction mixture is stirred in 30 ml ice water and made basic with cold ammonia solution. The precipitate formed is suction filtered, washed with water and dried. The crude product is extracted with petroleum ether and diethyl ether, suction filtered and dried. The product is purified by chromatography (10 g Chromabond SiOH-cartridge). 140.0 mg of the product are obtained as a powder (m.p 244°-248° C.).

Workup

  1. customThe precipitate formed
  2. filtrationfiltered
  3. washwashed with water
  4. customdried
  5. extractionThe crude product is extracted with petroleum ether and diethyl ether, suction
  6. filtrationfiltered
  7. customdried
  8. customThe product is purified by chromatography (10 g Chromabond SiOH-cartridge)

Sources & evidence

ORD record
ord-417cf5e793d94cfeb722f557eae425a7
Source dataset
uspto-grants-2014_09
Patent number
US08822474B2

Reaction notes

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