Benzoyl chloride → HCID 59244714, compound

HRID 912172Notes

Reaction equation

HRID 912172 reaction equation
COC1C=CC(CN(CC2C=CC(OC)=CC=2)C2N=CC(C3C4CCNC=4N=C(N4CCOCC4)N=3)=CN=2)=CC=1.C(Cl)(=O)C1C=CC=CC=1.COC1C=CC(C[N:57](CC2C=CC(OC)=CC=2)[C:58]2[N:63]=[CH:62][C:61]([C:64]3[C:65]4[CH2:78][CH2:77][N:76]([C:79]([C:81]5[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=5)=[O:80])[C:66]=4[N:67]=[C:68]([N:70]4[CH2:75][CH2:74][O:73][CH2:72][CH2:71]4)[N:69]=3)=[CH:60][N:59]=2)=CC=1>>[NH2:57][C:58]1[N:63]=[CH:62][C:61]([C:64]2[C:65]3[CH2:78][CH2:77][N:76]([C:79]([C:81]4[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=4)=[O:80])[C:66]=3[N:67]=[C:68]([N:70]3[CH2:75][CH2:74][O:73][CH2:72][CH2:71]3)[N:69]=2)=[CH:60][N:59]=1

Participants

4

Reactant 3

HCID 7412Benzoyl chlorideHCID 45258862Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amineHCID 67385172HCID 67385172, compound

Product 1

HCID 59244714HCID 59244714, compoundYield 20%

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 (50 mg) and benzoyl chloride (32 μl) instead of acetic anhydride, in the same manner as Example 1-D-01, a crude product of (4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-phenyl-methanone was obtained, and then the PMB groups were removed according to Deprotection method 1, to obtain the desired compound (D-27) as a yellow solid (3.8 mg, 20%).

Workup

  1. customthe PMB groups were removed

Sources & evidence

ORD record
ord-9d945ba0bb9f49b4bdf0ebb7f6793a3c
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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