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

HRID 912330Notes

Reaction equation

HRID 912330 reaction equation
COC1C=CC(CN(CC2C=CC(OC)=CC=2)C2N=CC(C3C4CCNC=4N=C(N4CCOCC4)N=3)=CN=2)=CC=1.CC1C=C(N2CCOCC2)C=CC=1N.[CH3:55][C:56]1[CH:61]=[C:60]([N:62]2[CH2:67][CH2:66][O:65][CH2:64][CH2:63]2)[CH:59]=[CH:58][C:57]=1[NH:68][C:69]([N:71]1[C:75]2[N:76]=[C:77]([N:105]3[CH2:110][CH2:109][O:108][CH2:107][CH2:106]3)[N:78]=[C:79]([C:80]3[CH:81]=[N:82][C:83]([N:86](CC4C=CC(OC)=CC=4)CC4C=CC(OC)=CC=4)=[N:84][CH:85]=3)[C:74]=2[CH2:73][CH2:72]1)=[O:70]>>[CH3:55][C:56]1[CH:61]=[C:60]([N:62]2[CH2:63][CH2:64][O:65][CH2:66][CH2:67]2)[CH:59]=[CH:58][C:57]=1[NH:68][C:69]([N:71]1[C:75]2[N:76]=[C:77]([N:105]3[CH2:110][CH2:109][O:108][CH2:107][CH2:106]3)[N:78]=[C:79]([C:80]3[CH:81]=[N:82][C:83]([NH2:86])=[N:84][CH:85]=3)[C:74]=2[CH2:73][CH2:72]1)=[O:70]

Participants

4

Reactant 3

HCID 219550002-Methyl-4-(morpholin-4-yl)anilineHCID 45258862Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amineHCID 866401344-{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-4-morpholin-4-yl-phenyl)-amide

Product 1

HCID 592445094-(2-Amino-pyrimidin-5-yl)-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid (2-methyl-4-morpholin-4-yl-phenyl)-amideYield 63%

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 (100 mg) and 2-methyl-4-morpholin-4-yl-phenylamine (39 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-4-morpholin-4-yl-phenyl)-amide was obtained as a crude product. Using 195 mg of this compound, PMB group was removed according to Deprotection method 2, to obtain the desired compound (D-240) (90 mg, 63%).

Workup

  1. customwas removed

Sources & evidence

ORD record
ord-09dc64b4b33048648e2f00e077d7e9bd
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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