1-Methylpiperazine → 4-(2-Amino-pyrimidin-5-yl)-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid [2-methyl-4-(4-methyl-piperazin-1-yl)-phenyl]-amide

HRID 912331Notes

Reaction equation

HRID 912331 reaction equation
COC1C=CC(CN(CC2C=CC(OC)=CC=2)C2N=CC(C3C4CCNC=4N=C(N4CCOCC4)N=3)=CN=2)=CC=1.CC1C=C(N2CCN(C)CC2)C=CC=1N.CN1CCNCC1.CC1C=CC(N2CCOCC2)=CC=1N.[CH3:77][C:78]1[CH:83]=[C:82]([N:84]2[CH2:89][CH2:88][N:87]([CH3:90])[CH2:86][CH2:85]2)[CH:81]=[CH:80][C:79]=1[NH:91][C:92]([N:94]1[C:98]2[N:99]=[C:100]([N:128]3[CH2:133][CH2:132][O:131][CH2:130][CH2:129]3)[N:101]=[C:102]([C:103]3[CH:104]=[N:105][C:106]([N:109](CC4C=CC(OC)=CC=4)CC4C=CC(OC)=CC=4)=[N:107][CH:108]=3)[C:97]=2[CH2:96][CH2:95]1)=[O:93]>>[CH3:77][C:78]1[CH:83]=[C:82]([N:84]2[CH2:89][CH2:88][N:87]([CH3:90])[CH2:86][CH2:85]2)[CH:81]=[CH:80][C:79]=1[NH:91][C:92]([N:94]1[C:98]2[N:99]=[C:100]([N:128]3[CH2:133][CH2:132][O:131][CH2:130][CH2:129]3)[N:101]=[C:102]([C:103]3[CH:104]=[N:105][C:106]([NH2:109])=[N:107][CH:108]=3)[C:97]=2[CH2:96][CH2:95]1)=[O:93]

Participants

6

Reactant 5

HCID 531671-MethylpiperazineHCID 21168682-Methyl-4-(4-methylpiperazin-1-yl)anilineHCID 392386232-Methyl-5-morpholinoanilineHCID 45258862Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amineHCID 866401354-{2-[Bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid [2-methyl-4-(4-methyl-piperazin-1-yl)-phenyl]-amide

Product 1

HCID 592448984-(2-Amino-pyrimidin-5-yl)-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid [2-methyl-4-(4-methyl-piperazin-1-yl)-phenyl]-amideYield 75%

Procedure

Using bis-(4-methoxy-benzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine (150 mg), and 2-methyl-4-(4-methyl-piperazin-1-yl)-phenylamine (63 mg) obtained using 1-methyl-piperazine instead of morpholine in the same manner as Step A and Step B in Example 1-D-240, instead of 2-methyl-5-morpholin-4-yl-phenylamine, in the same manner as Step C in Example 1-D-237, 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 [2-methyl-4-(4-methyl-piperazin-1-yl)-phenyl]-amide was obtained as a crude product. The PMB groups were removed according to Deprotection method 2, to obtain the desired compound (D-241) (110 mg, 75%).

Workup

  1. customobtained
  2. customThe PMB groups were removed

Sources & evidence

ORD record
ord-5e2f6d8232de4ea6ad09b795d6e564cb
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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