Morpholine → HCID 782859, compound
Reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[Br:10].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:4][C:3]=1[Br:10]Participants
Procedure
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).
Sources & evidence
- ORD record
- ord-99b7b6ef551b4d3f9df70bff27c7f243
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08022205B2
Reaction notes
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