Morpholine → 4-(3-Bromo-4-fluorobenzyl)morpholine

Participants

Reaction Steps

In the same manner as Step B in Example 1-D-26, using 4-fluoro-3-bromo-benzaldehyde (270 mg) and morpholine (0.23 ml), reductive amination was carried out, to obtain a crude product of 2-fluoro-5-morpholin-4-ylmethyl-bromobenzene as a colorless oil (344 mg). In the same manner as Example 1-D-08, bis-(4-methoxy-benzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine (92 mg) and using a crude product (66 mg) of 2-fluoro-5-morpholin-4-ylmethyl-bromobenzene obtained in the above step instead of 4-bromobenzoic acid methyl ester, a crude product of 5-[7-(2-fluoro-5-morpholin-4-ylmethyl-phenyl)-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]-pyrimidin-2-yl-bis-(4-methoxy-benzyl)-amine was obtained. Using a crude product (90 mg) of 5-[7-(2-fluoro-5-morpholin-4-ylmethyl-phenyl)-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]-pyrimidin-2-yl-bis-(4-methoxy-benzyl)-amine, according to the above Deprotection method 2, 5-[7-(2-fluoro-5-morpholin-4-ylmethyl-phenyl)-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]-pyrimidin-2-ylamine was obtained as a colorless powder (5.4 mg).

Provenance & Evidence