1-(2-Hydroxyethyl)piperazine → 4-(2-Amino-pyrimidin-5-yl)-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid methyl-{3-[methyl-(2-morpholin-4-yl-ethyl)-amino]-phenyl}-amide

HRID 912317Notes

Reaction equation

HRID 912317 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]([CH3:51])[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:5]=C[CH:7]=1.[CH3:52][NH:53][CH2:54][CH2:55][N:56]1[CH2:61][CH2:60][O:59][CH2:58][CH2:57]1.N1(CCO)CCNC[CH2:63]1.CN(CCN1CCOCC1)C1C=C(NC(N2C3N=C(N4CCOCC4)N=C(C4C=NC(N(CC5C=CC(OC)=CC=5)CC5C=CC(OC)=CC=5)=NC=4)C=3CC2)=O)C=CC=1>>[CH3:51][N:8]([C:4]1[CH:3]=[CH:2][CH:7]=[C:52]([N:53]([CH3:63])[CH2:54][CH2:55][N:56]2[CH2:61][CH2:60][O:59][CH2:58][CH2:57]2)[CH:5]=1)[C:9]([N:11]1[C:15]2[N:16]=[C:17]([N:45]3[CH2:50][CH2:49][O:48][CH2:47][CH2:46]3)[N:18]=[C:19]([C:20]3[CH:25]=[N:24][C:23]([NH2:26])=[N:22][CH:21]=3)[C:14]=2[CH2:13][CH2:12]1)=[O:10]

Participants

5

Reactant 4

HCID 76771-(2-Hydroxyethyl)piperazineHCID 14979282Methyl(2-(morpholin-4-yl)ethyl)amineHCID 592449624-{2-[Bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid (3-bromo-phenyl)-methyl-amideHCID 866401314-{2-[Bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {3-[methyl-(2-morpholin-4-yl-ethyl)-amino]-phenyl}-amide

Product 1

HCID 592443344-(2-Amino-pyrimidin-5-yl)-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid methyl-{3-[methyl-(2-morpholin-4-yl-ethyl)-amino]-phenyl}-amideYield 22%

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 (3-bromo-phenyl)-methyl-amide (112 mg) and methyl-(2-morpholin-4-yl-ethyl)-amine (25.8 mg) obtained in Step A in Example 1-D-139 instead of 2-piperazin-1-yl-ethanol, in the same manner as Step C in Example 1-D-153, 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 {3-[methyl-(2-morpholin-4-yl-ethyl)-amino]-phenyl}-amide was obtained as a crude product. The PMB groups were removed according to Deprotection method 3, to obtain the desired compound (D-227) as a brown solid (18.6 mg, 22%).

Workup

  1. customThe PMB groups were removed

Sources & evidence

ORD record
ord-1db9ad1d9ee84ffe8d688770d91eb2d6
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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