(4-Bromo-3-methyl-phenyl)-(4-methyl-piperazin-1-yl)-methanone → 1-FORMYL-4-METHYLPIPERAZINE

HRID 912259Notes

Reaction equation

COC1C=CC(CN(CC2C=CC(OC)=CC=2)C2N=CC(C3C4CCNC=4N=C(N4CCOCC4)N=3)=CN=2)=CC=1.BrC1C=CC([C:48]([N:50]2[CH2:55][CH2:54][N:53]([CH3:56])[CH2:52][CH2:51]2)=[O:49])=CC=1C>>[CH3:56][N:53]1[CH2:54][CH2:55][N:50]([CH:48]=[O:49])[CH2:51][CH2:52]1

Participants

Reactant 2

HCID 21093759(4-Bromo-3-methyl-phenyl)-(4-methyl-piperazin-1-yl)-methanone

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 32692211-FORMYL-4-METHYLPIPERAZINE

Procedure

Using 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) and (4-bromo-3-methyl-phenyl)-(4-methyl-piperazin-1-yl)-methanone (167 mg) instead of 4-chloropicolinic acid t-butylamide, in the same manner as Example 1-D-07, a crude product of 4-(4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-3-methyl-phenyl]-(4-methyl-piperazin-1-yl)-methanone was obtained, and then the PMB groups were removed according to the above Deprotection method 3, to obtain the desired compound (D-142) as a pale yellow powder (25 mg, 26%).

Sources & evidence

ORD record: ord-73336789d91e4234a822f976f82ca8da
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022205B2

Reaction notes

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