1,2-Dichloroethane → HCID 24936349, compound

HRID 888941Notes

Reaction equation

HRID 888941 reaction equation
Cl.Cl.[N:3]1[CH:8]=[CH:7][CH:6]=[N:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.Cl[C:16]1[N:17]=[C:18]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[C:19]2[S:24][C:23]([CH:25]=O)=[CH:22][C:20]=2[N:21]=1.C([N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])C.C(O[BH-](O[C:50](=O)[CH3:51])OC(=O)C)(=O)C.[Na+].Cl[CH2:55][CH2:56]Cl>ClCCl.C(O)(=O)C>[NH:35]1[C:36]2[C:37](=[C:55]([C:16]3[N:17]=[C:18]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[C:19]4[S:24][C:23]([CH2:25][N:12]5[CH2:13][CH2:14][N:9]([C:4]6[N:5]=[CH:6][CH:7]=[CH:8][N:3]=6)[CH2:10][CH2:11]5)=[CH:22][C:20]=4[N:21]=3)[CH:56]=[CH:50][CH:51]=2)[CH:39]=[CH:38]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 116802722-Piperazinylpyrimidine dihydrochlorideHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 24936349HCID 24936349, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(2-pyrimidyl)piperazine dihydrochloride (0.218 g), 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (0.20 g) and triethylamine (0.28 ml) in 1,2-dichloroethane (3 ml) was stirred for 1 hour. Acetic acid (0.040 ml) and sodium triacetoxyborohydride (0.195 g) were then added. After stirring for 24 hours the reaction mixture was diluted with dichloromethane, washed with sodium bicarbonate solution, dried (MgSO4) and the solvent removed in vacuo. The residue was purified by flash chromatography to 2-chloro-4-morpholin-4-yl-6-(4-pyrimidin-2-yl-piperazin-1-ylmethyl)-thieno[3,2-d]pyrimidine (0.115 g). 2-(1H-Indol-4-yl)-4-morpholin-4-yl-6-(4-pyrimidin-2-yl-piperazin-1-ylmethyl)-thieno[3,2-d]pyrimidine was prepared using the standard Suzuki coupling.

Workup

  1. stirringAfter stirring for 24 hours the reaction mixture
  2. washwashed with sodium bicarbonate solution
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by flash chromatography to 2-chloro-4-morpholin-4-yl-6-(4-pyrimidin-2-yl-piperazin-1-ylmethyl)-thieno[3,2-d]pyrimidine (0.115 g)

Sources & evidence

ORD record
ord-b610ff3a186e49e5bc965356d729c312
Source dataset
uspto-grants-2012_08
Patent number
US08252792B2

Reaction notes

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