Pyridine → HCID 59244831, compound

HRID 912144Notes

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.N1C=CC=CC=1.[C:51](OC(=O)C)(=[O:53])[CH3:52].[Cl-].[NH4+]>>[CH3:42][O:41][C:38]1[CH:37]=[CH:36][C:35]([CH2:34][N:12]([CH2:11][C:10]2[CH:9]=[CH:8][C:7]([O:6][CH3:5])=[CH:44][CH:43]=2)[C:13]2[N:14]=[CH:15][C:16]([C:19]3[C:20]4[CH2:33][CH2:32][N:31]([C:51](=[O:53])[CH3:52])[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:17][N:18]=2)=[CH:40][CH:39]=1

Participants

Reactant 5

HCID 1049Pyridine

HCID 63651,1-Dichloroethane

HCID 7918Acetic Anhydride

HCID 25517Ammonium Chloride

HCID 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 59244831HCID 59244831, compound

Procedure

To 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, 0.185 mmol), pyridine (45 μl, 0.556 mmol) and N,N-dimethylaminopyridine (2.3 mg, 0.0185 mmol) were added, and further acetic anhydride (52 μl, 0.556 mmol) was added, followed by refluxing for 3 hours. This was cooled to room temperature, followed by addition of saturated aqueous ammonium chloride solution, and passed through Whatman tube. The resulting organic phase was concentrated under reduced pressure, to obtain 1-(4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-ethanone as a crude product. To this, TFA (2 ml) and concentrated sulfuric acid (2 drops) were added, followed by stirring at 40° C. for 4 hours. After concentration of TFA under reduced pressure, water was added, followed by neutralization with 1M aqueous sodium hydroxide solution. After filtering the solid, dichloromethane (5 ml) was added, followed by stirring at room temperature for 30 minutes, and the solid was filtered off, to obtain the desired compound as a colorless solid (29.3 mg, yield 46%).

Workup

temperatureby refluxing for 3 hours
concentrationThe resulting organic phase was concentrated under reduced pressure

Sources & evidence

ORD record: ord-7c904cb484714e1b87d3e012ee9fafa3
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022205B2

Reaction notes

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