1,1-Dichloroethane → HCID 59244836, compound

HRID 912210Notes

Reaction equation

HRID 912210 reaction equation
ClC(Cl)C.[CH3:5][O:6][C:7]1[CH:44]=[CH:43][C:10]([CH2:11][N:12]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=2)[C:13]2[N:18]=[CH:17][C:16]([C:19]3[C:20]4[CH2:33][CH2:32][NH:31][C:21]=4[N:22]=[C:23]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[N:24]=3)=[CH:15][N:14]=2)=[CH:9][CH:8]=1.[I:45][C:46]1[CH:51]=[CH:50][CH:49]=[C:48]([N:52]=[C:53]=[O:54])[CH:47]=1>CN(C1C=CN=CC=1)C.ClCCl>[I:45][C:46]1[CH:47]=[C:48]([NH:52][C:53]([N:31]2[C:21]3[N:22]=[C:23]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[N:24]=[C:19]([C:16]4[CH:15]=[N:14][C:13]([N:12]([CH2:11][C:10]5[CH:9]=[CH:8][C:7]([O:6][CH3:5])=[CH:44][CH:43]=5)[CH2:34][C:35]5[CH:36]=[CH:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=5)=[N:18][CH:17]=4)[C:20]=3[CH2:33][CH2:32]2)=[O:54])[CH:49]=[CH:50][CH:51]=1

Participants

6

Reactant 3

HCID 63651,1-DichloroethaneHCID 44990001-Iodo-3-isocyanatobenzeneHCID 45258862Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine

Product 1

HCID 59244836HCID 59244836, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a dichloroethane solution (10 ml) of bis-(4-methoxy-benzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine (540 mg), DMAP (12.2 mg) and 1-iodo-3-isocyanato-benzene (490 mg) were added, followed by refluxing for 17 hours. This was cooled to room temperature, and dichloromethane (40 ml) was added. After washing with saturated aqueous ammonium chloride solution (30 ml), the organic layer was dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was distilled off under reduced pressure, followed by silica gel column chromatography (hexane/dichloromethane/ethyl acetate=4/4/1 to 1/2/1), to obtain the desired compound as a crude product (404 mg, 51%).

Workup

  1. temperatureby refluxing for 17 hours
  2. washAfter washing with saturated aqueous ammonium chloride solution (30 ml)
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationAfter the sodium sulfate was filtered off
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8dd169bf21304e31a049bd009d2e54f2
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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