1-Ethylpiperazine → 4-(2-aminopyrimidin-5-yl)-N-[4-(4-ethylpiperazin-1-yl)-2-methylphenyl]-2-morpholin-4-yl-5,6-dihydropyrrolo[2,3-d]pyrimidine-7-carboxamide

HRID 912332Notes

Reaction equation

HRID 912332 reaction equation
COC1C=CC(CN(CC2C=CC(OC)=CC=2)C2N=CC(C3C4CCNC=4N=C(N4CCOCC4)N=3)=CN=2)=CC=1.C(N1CCN(C2C=CC(N)=C(C)C=2)CC1)C.C(N1CCNCC1)C.CC1C=CC(N2CCOCC2)=CC=1N.[CH2:79]([N:81]1[CH2:86][CH2:85][N:84]([C:87]2[CH:92]=[CH:91][C:90]([NH:93][C:94]([N:96]3[C:100]4[N:101]=[C:102]([N:130]5[CH2:135][CH2:134][O:133][CH2:132][CH2:131]5)[N:103]=[C:104]([C:105]5[CH:106]=[N:107][C:108]([N:111](CC6C=CC(OC)=CC=6)CC6C=CC(OC)=CC=6)=[N:109][CH:110]=5)[C:99]=4[CH2:98][CH2:97]3)=[O:95])=[C:89]([CH3:136])[CH:88]=2)[CH2:83][CH2:82]1)[CH3:80]>>[CH2:79]([N:81]1[CH2:86][CH2:85][N:84]([C:87]2[CH:92]=[CH:91][C:90]([NH:93][C:94]([N:96]3[C:100]4[N:101]=[C:102]([N:130]5[CH2:131][CH2:132][O:133][CH2:134][CH2:135]5)[N:103]=[C:104]([C:105]5[CH:110]=[N:109][C:108]([NH2:111])=[N:107][CH:106]=5)[C:99]=4[CH2:98][CH2:97]3)=[O:95])=[C:89]([CH3:136])[CH:88]=2)[CH2:83][CH2:82]1)[CH3:80]

Participants

6

Reactant 5

HCID 791961-EthylpiperazineHCID 21253244-(4-Ethylpiperazin-1-yl)-2-methylanilineHCID 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 866401364-{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-(4-ethyl-piperazin-1-yl)-2-methyl-phenyl]-amide

Product 1

HCID 592444084-(2-aminopyrimidin-5-yl)-N-[4-(4-ethylpiperazin-1-yl)-2-methylphenyl]-2-morpholin-4-yl-5,6-dihydropyrrolo[2,3-d]pyrimidine-7-carboxamideYield 76%

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 4-(4-ethyl-piperazin-1-yl)-2-methyl-phenylamine (67 mg) obtained using 1-ethyl-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 [4-(4-ethyl-piperazin-1-yl)-2-methyl-phenyl]-amide was obtained as a crude product. The PMB groups were removed according to Deprotection method 2, to obtain the desired compound (D-242) (110 mg, 76%).

Workup

  1. customobtained
  2. customThe PMB groups were removed

Sources & evidence

ORD record
ord-734fb4cc1c134bad86f69be06ba895d0
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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