Diisopropylethylamine → {7-Bromo-2-[4-(4-chlorophenyl)piperazin-1-yl]thieno[3,2-d]pyrimidin-4-yl}propylamine

HRID 1788033Notes

Reaction equation

HRID 1788033 reaction equation
[Br:1][C:2]1[C:6]2[N:7]=[C:8](Cl)[N:9]=[C:10]([CH2:11][CH2:12][CH2:13][NH2:14])[C:5]=2[S:4][CH:3]=1.[ClH:16].ClC1N=[C:20]([NH:27][CH:28]2C[CH2:32][CH2:31][NH:30][CH2:29]2)[C:21]2S[CH2:25][CH2:24][C:22]=2N=1.[CH:34](N(C(C)C)CC)(C)C>O1CCOCC1>[Br:1][C:2]1[C:6]2[N:7]=[C:8]([N:30]3[CH2:29][CH2:28][N:27]([C:20]4[CH:21]=[CH:22][C:24]([Cl:16])=[CH:25][CH:34]=4)[CH2:32][CH2:31]3)[N:9]=[C:10]([CH2:11][CH2:12][CH2:13][NH2:14])[C:5]=2[S:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 86616275(2-Chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)piperidin-3-ylamine hydrochlorideHCID 86616282HCID 86616282, compound

Product 1

HCID 86616283{7-Bromo-2-[4-(4-chlorophenyl)piperazin-1-yl]thieno[3,2-d]pyrimidin-4-yl}propylamineYield 110.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

2.00 g (6.20 mmol) of (7-bromo-2-chlorothieno[3,2-d]pyrimidin-4-yl)propylamine (V), 4.64 g (23.59 mmol) of 1-(4-chlorophenyl)piperazine (VI), and 2.13 mL (12.39 mmol) of diisopropylethylamine are placed in 15 mL of dioxane and heated to 100° C. in the microwave for 0.75 hours. As only 50% reacted, the reaction mixture is heated to 160° C. in the microwave for another 1.5 hours. Then the precipitate formed is suction filtered, washed with water, and stirred with petroleum ether. After suction filtering again, 3.19 g of product VII (100%) is obtained.

Workup

  1. customAs only 50% reacted
  2. temperaturethe reaction mixture is heated to 160° C. in the microwave for another 1.5 hours
  3. customThen the precipitate formed
  4. filtrationfiltered
  5. washwashed with water
  6. filtrationAfter suction filtering again

Sources & evidence

ORD record
ord-af0e7afdd38e4262812b58424aba8782
Source dataset
uspto-grants-2009_03
Patent number
US07511045B2

Reaction notes

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