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

HRID 912336Notes

Reaction equation

HRID 912336 reaction equation
COC1C=CC(CN(CC2C=CC(OC)=CC=2)C2N=CC(C3C4CCNC=4N=C(N4CCOCC4)N=3)=CN=2)=CC=1.NC1C(C)=C(C(N2CCN(CC)CC2)=O)C=CC=1.C(N1CCNCC1)C.CC1C=CC(N2CCOCC2)=CC=1N.[CH2:81]([N:83]1[CH2:88][CH2:87][N:86]([C:89]([C:91]2[C:92]([CH3:140])=[C:93]([NH:97][C:98]([N:100]3[C:104]4[N:105]=[C:106]([N:134]5[CH2:139][CH2:138][O:137][CH2:136][CH2:135]5)[N:107]=[C:108]([C:109]5[CH:110]=[N:111][C:112]([N:115](CC6C=CC(OC)=CC=6)CC6C=CC(OC)=CC=6)=[N:113][CH:114]=5)[C:103]=4[CH2:102][CH2:101]3)=[O:99])[CH:94]=[CH:95][CH:96]=2)=[O:90])[CH2:85][CH2:84]1)[CH3:82]>>[CH2:81]([N:83]1[CH2:88][CH2:87][N:86]([C:89]([C:91]2[C:92]([CH3:140])=[C:93]([NH:97][C:98]([N:100]3[C:104]4[N:105]=[C:106]([N:134]5[CH2:135][CH2:136][O:137][CH2:138][CH2:139]5)[N:107]=[C:108]([C:109]5[CH:114]=[N:113][C:112]([NH2:115])=[N:111][CH:110]=5)[C:103]=4[CH2:102][CH2:101]3)=[O:99])[CH:94]=[CH:95][CH:96]=2)=[O:90])[CH2:85][CH2:84]1)[CH3:82]

Participants

6

Reactant 5

HCID 791961-EthylpiperazineHCID 16795409HCID 16795409, compoundHCID 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 86640139HCID 86640139, compound

Product 1

HCID 592447534-(2-Amino-pyrimidin-5-yl)-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid [3-(4-ethyl-piperazine-1-carbonyl)-2-methyl-phenyl]-amideYield 28%

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 (3-amino-2-methyl-phenyl)-(4-ethyl-piperazin-1-yl)-methanone (76 mg) obtained using 1-ethyl-piperazine instead of morpholine in the same manner as Step A and Step B in Example 1-D-243, 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 [3-(4-ethyl-piperazine-1-carbonyl)-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-245) (45 mg, 28%).

Workup

  1. customobtained
  2. customThe PMB groups were removed

Sources & evidence

ORD record
ord-ade95223faf94f1d9a75adf242dc6d0b
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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