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

HRID 912328Notes

Reaction equation

HRID 912328 reaction equation
C(N1CCN(C2C=CC(C)=C(N)C=2)CC1)C.C(N1CCNCC1)C.CC1C=CC(N2CCOCC2)=CC=1N.COC1C=CC(CN(CC2C=CC(OC)=CC=2)C2N=CC(C3C4CCNC=4N=C(N4CCOCC4)N=3)=CN=2)=CC=1.[CH2:79]([N:81]1[CH2:86][CH2:85][N:84]([C:87]2[CH:88]=[CH:89][C:90]([CH3:136])=[C:91]([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])[CH:92]=2)[CH2:83][CH2:82]1)[CH3:80]>>[CH2:79]([N:81]1[CH2:86][CH2:85][N:84]([C:87]2[CH:88]=[CH:89][C:90]([CH3:136])=[C:91]([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])[CH:92]=2)[CH2:83][CH2:82]1)[CH3:80]

Participants

6

Reactant 5

HCID 791961-EthylpiperazineHCID 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 629105465-(4-Ethyl-1-piperazinyl)-2-methylbenzenamineHCID 866401334-{2-[Bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid [5-(4-ethyl-piperazin-1-yl)-2-methyl-phenyl]-amide

Product 1

HCID 592443284-(2-Amino-pyrimidin-5-yl)-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid [5-(4-ethyl-piperazin-1-yl)-2-methyl-phenyl]-amide

Procedure

Using 5-(4-ethyl-piperazin-1-yl)-2-methyl-phenylamine (73 mg) obtained using 1-ethyl-piperazine instead of morpholine in the same manner as Step A and Step B in Example 1-D-237, instead of 2-methyl-5-morpholin-4-yl-phenylamine, 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 (200 mg), 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 [5-(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-239) as an ivory solid (62 mg, 41%).

Workup

  1. customobtained
  2. customThe PMB groups were removed

Sources & evidence

ORD record
ord-95cc88dc5b294baa8b33efd7faf2f18a
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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