926267-12-1 → HCID 59244696, compound

HRID 912334Notes

Reaction equation

HRID 912334 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(N2CCOCC2)=O)C=CC=1.[CH3:57][C:58]1[C:63]([C:64]([N:66]2[CH2:71][CH2:70][O:69][CH2:68][CH2:67]2)=[O:65])=[CH:62][CH:61]=[CH:60][C:59]=1[NH:72][C:73]([N:75]1[C:79]2[N:80]=[C:81]([N:109]3[CH2:114][CH2:113][O:112][CH2:111][CH2:110]3)[N:82]=[C:83]([C:84]3[CH:85]=[N:86][C:87]([N:90](CC4C=CC(OC)=CC=4)CC4C=CC(OC)=CC=4)=[N:88][CH:89]=3)[C:78]=2[CH2:77][CH2:76]1)=[O:74]>>[CH3:57][C:58]1[C:63]([C:64]([N:66]2[CH2:67][CH2:68][O:69][CH2:70][CH2:71]2)=[O:65])=[CH:62][CH:61]=[CH:60][C:59]=1[NH:72][C:73]([N:75]1[C:79]2[N:80]=[C:81]([N:109]3[CH2:114][CH2:113][O:112][CH2:111][CH2:110]3)[N:82]=[C:83]([C:84]3[CH:85]=[N:86][C:87]([NH2:90])=[N:88][CH:89]=3)[C:78]=2[CH2:77][CH2:76]1)=[O:74]

Participants

4

Reactant 3

HCID 16770980926267-12-1HCID 45258862Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amineHCID 86640137HCID 86640137, compound

Product 1

HCID 59244696HCID 59244696, compoundYield 40%

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)-morpholin-4-yl-methanone (67 mg) obtained in Step B 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-3-(morpholine-4-carbonyl)-phenyl]-amide was obtained as a crude product. The PMB groups were removed according to Deprotection method 2, to obtain the desired compound (D-243) (60 mg, 40%).

Workup

  1. customThe PMB groups were removed

Sources & evidence

ORD record
ord-833cc9d5d5d44e219c3c17d640e9b10f
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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