4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → 4-(2-Amino-pyrimidin-5-yl)-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid (4-pyridin-4-yl-phenyl)-amide

HRID 912198Notes

Reaction equation

HRID 912198 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]2[C:15]3[N:16]=[C:17]([N:45]4[CH2:50][CH2:49][O:48][CH2:47][CH2:46]4)[N:18]=[C:19]([C:20]4[CH:21]=[N:22][C:23]([N:26](CC5C=CC(OC)=CC=5)CC5C=CC(OC)=CC=5)=[N:24][CH:25]=4)[C:14]=3[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:59]2[CH:64]=[CH:63][N:62]=[CH:61][CH:60]=2)O1>>[N:62]1[CH:63]=[CH:64][C:59]([C:2]2[CH:3]=[CH:4][C:5]([NH:8][C:9]([N:11]3[C:15]4[N:16]=[C:17]([N:45]5[CH2:46][CH2:47][O:48][CH2:49][CH2:50]5)[N:18]=[C:19]([C:20]5[CH:25]=[N:24][C:23]([NH2:26])=[N:22][CH:21]=5)[C:14]=4[CH2:13][CH2:12]3)=[O:10])=[CH:6][CH:7]=2)=[CH:60][CH:61]=1

Participants

3

Reactant 2

HCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 592448904-{2-[Bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid (4-iodo-phenyl)-amide

Product 1

HCID 592443824-(2-Amino-pyrimidin-5-yl)-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid (4-pyridin-4-yl-phenyl)-amide

Procedure

Using 4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid (4-iodo-phenyl)-amide (25 mg) obtained in Step A in Example 1-D-65 and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (13 mg) instead of pyridin-3-boronic acid, in the same manner as Step B in Example 1-D-65, 4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid-4-pyridin-4-yl-phenyl)-amide was obtained. Further, in the same manner as Step B in Example 1-D-65 according to the above Deprotection method 3, the PMB groups were removed, to obtain the desired compound (D-66) as a colorless solid (8.9 mg, 40%).

Workup

  1. customthe PMB groups were removed

Sources & evidence

ORD record
ord-e9e6bf9192a54bad903a0e4f3b00314a
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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