HCID 67386071, compound → Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine

HRID 912179Notes

Reaction equation

HRID 912179 reaction equation
BrC1C=CC([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)=NC=1.FC1N=CC(N2C3N=C(N4CCOCC4)N=C(C4C=NC(N(CC5C=CC(OC)=CC=5)CC5C=CC(OC)=CC=5)=NC=4)C=3CC2)=CC=1>FC1C=CC(Br)=CN=1>[CH3:41][O:40][C:37]1[CH:36]=[CH:35][C:34]([CH2:33][N:23]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)[C:20]2[N:21]=[CH:22][C:17]([C:16]3[C:11]4[CH2:10][CH2:9][NH:8][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:18][N:19]=2)=[CH:39][CH:38]=1

Participants

4

Reactant 2

HCID 67386071HCID 67386071, compoundHCID 67386401HCID 67386401, compound

Product 1

HCID 45258862Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine

Reagents, catalysts & solvents 1

HCID 27831685-Bromo-2-fluoropyridineSolvent

Procedure

From bis-(4-methoxy-benzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine (81 mg) and 2-fluoro-5-bromopyridine (30 μl), in the same manner as Step B in Example 1-D-25, crude products of {5-[7-(5-bromo-pyridin-2-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 {5-[7-(6-fluoro-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 were obtained, and then for each products the PMB groups were removed according to Deprotection method 3, to obtain the desired compound (D-36) as a colorless powder (5 mg, 32%) and as a colorless powder (D-37: 7 mg, 63%).

Sources & evidence

ORD record
ord-b7f9cf4e9c4a4c48a7102afb801a1dd3
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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