Morpholine → HCID 59244594, compound

HRID 912243Notes

Reaction equation

HRID 912243 reaction equation
COC1C=CC(CN(CC2C=CC(OC)=CC=2)C2N=CC(C3C4CCN(C5C=CC(C=O)=CC=5)C=4N=C(N4CCOCC4)N=3)=CN=2)=CC=1.N1CCOCC1.COC1C=CC(C[N:62](CC2C=CC(OC)=CC=2)[C:63]2[N:68]=[CH:67][C:66]([C:69]3[C:70]4[CH2:83][CH2:82][N:81]([C:84]5[CH:89]=[CH:88][C:87]([CH2:90][N:91]6[CH2:96][CH2:95][O:94][CH2:93][CH2:92]6)=[CH:86][CH:85]=5)[C:71]=4[N:72]=[C:73]([N:75]4[CH2:80][CH2:79][O:78][CH2:77][CH2:76]4)[N:74]=3)=[CH:65][N:64]=2)=CC=1>>[N:75]1([C:73]2[N:74]=[C:69]([C:66]3[CH:67]=[N:68][C:63]([NH2:62])=[N:64][CH:65]=3)[C:70]3[CH2:83][CH2:82][N:81]([C:84]4[CH:89]=[CH:88][C:87]([CH2:90][N:91]5[CH2:92][CH2:93][O:94][CH2:95][CH2:96]5)=[CH:86][CH:85]=4)[C:71]=3[N:72]=2)[CH2:76][CH2:77][O:78][CH2:79][CH2:80]1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 59244394HCID 59244394, compoundHCID 67385585HCID 67385585, compound

Product 1

HCID 59244594HCID 59244594, compound

Procedure

Using 4-(4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-benzaldehyde (70 mg) and morpholine (14 μl) instead of 1-methylpiperazine, in the same manner as Step B in Example 1-D-26, a crude product of bis-(4-methoxy-benzyl)-{5-[2-morpholin-4-yl-7-(4-morpholin-4-ylmethyl-phenyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]-pyrimidin-2-yl}-amine was obtained, and then the PMB groups were removed according to the above Deprotection method 3, to obtain the desired compound (D-126) as a pale brown powder (26 mg, 50%).

Workup

  1. customthe PMB groups were removed

Sources & evidence

ORD record
ord-d1a00d9913b348408f86f000c0428f1e
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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