Trifluoroacetic acid → 5-(2-Morpholin-4-yl-7-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-ylamine

HRID 912112Notes

Reaction equation

COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[N:14]=[CH:13][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][N:27]([C:30]5[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=5)[C:17]=4[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=3)=[CH:11][N:10]=2)=CC=1.C(O)(C(F)(F)F)=O>S(=O)(=O)(O)O>[N:21]1([C:19]2[N:20]=[C:15]([C:12]3[CH:13]=[N:14][C:9]([NH2:8])=[N:10][CH:11]=3)[C:16]3[CH2:29][CH2:28][N:27]([C:30]4[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=4)[C:17]=3[N:18]=2)[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1

Participants

Conditions

Temperature: 40 °C

Procedure

To the obtained bis-(4-methoxy-benzyl)-[5-(2-morpholin-4-yl-7-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine, TFA (3 ml) and concentrated sulfuric acid (a few drops) were added, followed by stirring at 40° C. for 6 hours. This was concentrated under reduced pressure, and water was added, followed by neutralization with 1N aqueous sodium hydroxide solution. The resulting solid was purified by silica gel column chromatography (dichloromethane/2N ammonia methanol=40/1 to 10/1), to obtain the desired compound as a colorless solid (32.3 mg, yield 26%).

Workup

concentrationThis was concentrated under reduced pressure, and water
additionwas added
customThe resulting solid was purified by silica gel column chromatography (dichloromethane/2N ammonia methanol=40/1 to 10/1)

Sources & evidence

ORD record: ord-951a58ac118541fe83cb28e8ef2e71c3
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022205B2

Reaction notes

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