Allyl chloroformate → HCID 59244570, compound

HRID 912181Notes

Reaction equation

COC1C=CC(CN(CC2C=CC(OC)=CC=2)C2N=CC(C3C4CCNC=4N=C(N4CCOCC4)N=3)=CN=2)=CC=1.ClC(OCC=C)=O.[CH2:48]([O:51][C:52]([N:54]1[C:58]2[N:59]=[C:60]([N:88]3[CH2:93][CH2:92][O:91][CH2:90][CH2:89]3)[N:61]=[C:62]([C:63]3[CH:64]=[N:65][C:66]([N:69](CC4C=CC(OC)=CC=4)CC4C=CC(OC)=CC=4)=[N:67][CH:68]=3)[C:57]=2[CH2:56][CH2:55]1)=[O:53])[CH:49]=[CH2:50]>>[CH2:48]([O:51][C:52]([N:54]1[C:58]2[N:59]=[C:60]([N:88]3[CH2:89][CH2:90][O:91][CH2:92][CH2:93]3)[N:61]=[C:62]([C:63]3[CH:64]=[N:65][C:66]([NH2:69])=[N:67][CH:68]=3)[C:57]=2[CH2:56][CH2:55]1)=[O:53])[CH:49]=[CH2:50]

Participants

Reactant 3

HCID 18052Allyl chloroformate

HCID 45258862Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine

HCID 67385705HCID 67385705, compound

Product 1

HCID 59244570HCID 59244570, compoundYield 92%

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 (41.4 mg, 0.0769 mmol) and allyl chloroformate (17 μl, 0.160 mmol) 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]pyrimidine-7-carboxylic acid allyl ester was obtained, and deprotection was further carried out according to the above deprotection reaction method 1, to obtain the desired compound (D-40) as a colorless powder (27.0 mg, 92%).

Workup

customdeprotection was further carried out according to the above deprotection reaction method 1

Sources & evidence

ORD record: ord-9106e640203d43fca9cd1130b998f0c3
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022205B2

Reaction notes

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