4-chloro-2-morpholin-4-yl-7-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine → 4-Methyl-5-(2-morpholin-4-yl-7-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-ylamine

HRID 912347Notes

Reaction equation

HRID 912347 reaction equation
Cl[C:2]1[C:3]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[C:4]=2[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:7]=1.COC1C=CC(C[N:30](CC2C=CC(OC)=CC=2)[C:31]2[N:36]=[C:35]([CH3:37])[C:34](B3OC(C)(C)C(C)(C)O3)=[CH:33][N:32]=2)=CC=1.COC1C=CC(CN(CC2C=CC(OC)=CC=2)C2N=CC(B3OC(C)(C)C(C)(C)O3)=CN=2)=CC=1>>[CH3:37][C:35]1[C:34]([C:2]2[C:3]3[CH2:16][CH2:15][N:14]([C:17]4[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=4)[C:4]=3[N:5]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[N:7]=2)=[CH:33][N:32]=[C:31]([NH2:30])[N:36]=1

Participants

4

Reactant 3

HCID 592447084-chloro-2-morpholin-4-yl-7-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidineHCID 67385320Bis-(4-methoxybenzyl)-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidin-2-yl]amineHCID 67385762Bis-(4-methoxy-benzyl)-[4-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidin-2-yl]-amine

Product 1

HCID 592444234-Methyl-5-(2-morpholin-4-yl-7-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-ylamineYield 25%

Procedure

Using 4-chloro-2-morpholin-4-yl-7-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (64 mg) obtained in Step C in Example 1-B-01 and bis-(4-methoxy-benzyl)-[4-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidin-2-yl]-amine (105 mg) obtained in Step A in Example 1-D-260 instead of bis-(4-methoxy-benzyl)-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidin-2-yl]amine used in Step D in Example 1-B-01, the same operation as Step D in Example 1-B-01 was carried out, to obtain the desired compound (D-261) as a colorless powder (19 mg, 25%).

Sources & evidence

ORD record
ord-eafcb39f83894723b9700b0716b05cf0
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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