N-(3-Aminopropyl)morpholine → bis-(4-methoxy-benzyl)-(5-{2-morpholin-4-yl-7-[2-(3-morpholin-4-yl-propylamino)-pyridin-4-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}-pyrimidin-2-yl)-amine

HRID 912200Notes

Reaction equation

HRID 912200 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[C:12]3[N:13]=[C:14]([N:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)[N:15]=[C:16]([C:17]4[CH:18]=[N:19][C:20]([N:23]([CH2:33][C:34]5[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=5)[CH2:24][C:25]5[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=5)=[N:21][CH:22]=4)[C:11]=3[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.[NH2:48][CH2:49][CH2:50][CH2:51][N:52]1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1>>[CH3:32][O:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:23]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[C:20]2[N:19]=[CH:18][C:17]([C:16]3[C:11]4[CH2:10][CH2:9][N:8]([C:6]5[CH:5]=[CH:4][N:3]=[C:2]([NH:48][CH2:49][CH2:50][CH2:51][N:52]6[CH2:57][CH2:56][O:55][CH2:54][CH2:53]6)[CH:7]=5)[C:12]=4[N:13]=[C:14]([N:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)[N:15]=3)=[CH:22][N:21]=2)=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 61055N-(3-Aminopropyl)morpholineHCID 45258863HCID 45258863, compound

Product 1

HCID 67385724bis-(4-methoxy-benzyl)-(5-{2-morpholin-4-yl-7-[2-(3-morpholin-4-yl-propylamino)-pyridin-4-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}-pyrimidin-2-yl)-amineYield 42.5%

Procedure

Using {5-[7-(2-chloro-pyridin-4-yl)-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]-pyrimidin-2-yl}-bis-(4-methoxy-benzyl)-amine (200 mg, 0.31 mmol) obtained in Step A instead of {5-[7-(6-chloro-pyridin-3-yl)-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]-pyrimidin-2-yl}-bis-(4-methoxy-benzyl)-amine, and N-(3-aminopropyl)morpholine (54 μl, 0.37 mmol) instead of N,N,N′-trimethyl ethylenediamine, in the same manner as Step B in Example 1-D-48, amination was carried out, to obtain a crude product of bis-(4-methoxy-benzyl)-(5-{2-morpholin-4-yl-7-[2-(3-morpholin-4-yl-propylamino)-pyridin-4-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}-pyrimidin-2-yl)-amine as a yellow solid (100 mg), and then the PMB groups were removed according to the above Deprotection method 2, to obtain the desired compound (D-69) as a yellow powder (27 mg, 17%).

Sources & evidence

ORD record
ord-c012744f4aae42c69c6c89692c28981a
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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