1,1-Dichloroethane → HCID 59244910, compound

HRID 912174Notes

Reaction equation

HRID 912174 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.[CH2:45]([O:47][C:48](=[O:53])[CH2:49][N:50]=[C:51]=[O:52])[CH3:46].[Cl-].[NH4+]>C(N(CC)CC)C>[CH2:45]([O:47][C:48](=[O:53])[CH2:49][NH:50][C:51]([N:31]1[C:21]2[N:22]=[C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[N:24]=[C:19]([C:16]3[CH:15]=[N:14][C:13]([N:12]([CH2:11][C:10]4[CH:9]=[CH:8][C:7]([O:6][CH3:5])=[CH:44][CH:43]=4)[CH2:34][C:35]4[CH:36]=[CH:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=4)=[N:18][CH:17]=3)[C:20]=2[CH2:33][CH2:32]1)=[O:52])[CH3:46]

Participants

6

Reactant 4

HCID 63651,1-DichloroethaneHCID 25517Ammonium ChlorideHCID 76283Ethyl isocyanatoacetateHCID 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 59244910HCID 59244910, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a dichloroethane solution (2 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 (100 mg), triethylamine (260 μl) and isocyanato-acetic acid ethyl ester (208 μl) were added, followed by refluxing for 3 hours. After this was cooled to room temperature, saturated aqueous ammonium chloride solution was added, and passed through Whatman tube. The resulting organic layer was concentrated under reduced pressure, followed by purification by silica gel column chromatography (dichloromethane/methanol=/) column chromatography (dichloromethane/methanol=1/0 to 100/1), to obtain a crude product of the desired compound (127 mg, quant.).

Workup

  1. temperatureby refluxing for 3 hours
  2. concentrationThe resulting organic layer was concentrated under reduced pressure
  3. customfollowed by purification by silica gel column chromatography (dichloromethane/methanol=/) column chromatography (dichloromethane/methanol=1/0 to 100/1)

Sources & evidence

ORD record
ord-ddce7930f83242d4a6c1858416cc3598
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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