Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine → HCID 67385428, compound

HRID 912300Notes

Reaction equation

HRID 912300 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[CH:21]=[C:20](Cl)[CH:19]=[CH:18][N:17]=2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23][O:24][C:25]1[CH:62]=[CH:61][C:28]([CH2:29][N:30]([CH2:52][C:53]2[CH:58]=[CH:57][C:56]([O:59][CH3:60])=[CH:55][CH:54]=2)[C:31]2[N:36]=[CH:35][C:34]([C:37]3[C:38]4[CH2:51][CH2:50][NH:49][C:39]=4[N:40]=[C:41]([N:43]4[CH2:48][CH2:47][O:46][CH2:45][CH2:44]4)[N:42]=3)=[CH:33][N:32]=2)=[CH:27][CH:26]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[CH:21]=[C:20]([N:49]3[C:39]4[N:40]=[C:41]([N:43]5[CH2:44][CH2:45][O:46][CH2:47][CH2:48]5)[N:42]=[C:37]([C:34]5[CH:35]=[N:36][C:31]([N:30]([CH2:52][C:53]6[CH:58]=[CH:57][C:56]([O:59][CH3:60])=[CH:55][CH:54]=6)[CH2:29][C:28]6[CH:61]=[CH:62][C:25]([O:24][CH3:23])=[CH:26][CH:27]=6)=[N:32][CH:33]=5)[C:38]=4[CH2:51][CH2:50]3)[CH:19]=[CH:18][N:17]=2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 45258862Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amineHCID 592442111,1-Dimethylethyl 4-[(4-chloro-2-pyridinyl)carbonyl]-1-piperazinecarboxylate

Product 1

HCID 67385428HCID 67385428, compoundYield 57.7%

Procedure

Using 4-(4-chloro-pyridine-2-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester (163 mg, 0.500 mmol) obtained in Step A instead of 4-chloropicolinic acid t-butylamide, and bis-(4-methoxy-benzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine (245 mg, 445 mmol), in the same manner as Example 1-D-07, amination was carried out, to obtain a crude product of 4-[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)-pyridine-2-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester as a yellow solid (239 mg), and further PMB group and BOC group were removed according to the above Deprotection method 2, to obtain the desired compound (D-199) as a yellow powder (67 mg, 49%).

Sources & evidence

ORD record
ord-1cdfaec3cacc4b59827e0131bc10b100
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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