tert-Butyl piperazine-1-carboxylate → 4-(2-Amino-pyrimidin-5-yl)-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid methyl-(3-piperazin-1-yl-phenyl)-amide

HRID 912268Notes

Reaction equation

HRID 912268 reaction equation
BrC1C=C(N(C)C(N2C3N=C(N4CCOCC4)N=C(C4C=NC(N(CC5C=CC(OC)=CC=5)CC5C=CC(OC)=CC=5)=NC=4)C=3CC2)=O)C=CC=1.C(N1CCNCC1)(OC(C)(C)C)=O.C(OC([N:72]1[CH2:77][CH2:76][N:75]([C:78]2[CH:83]=[CH:82][CH:81]=[C:80]([N:84]([C:86]([N:88]3[C:92]4[N:93]=[C:94]([N:122]5[CH2:127][CH2:126][O:125][CH2:124][CH2:123]5)[N:95]=[C:96]([C:97]5[CH:98]=[N:99][C:100]([N:103](CC6C=CC(OC)=CC=6)CC6C=CC(OC)=CC=6)=[N:101][CH:102]=5)[C:91]=4[CH2:90][CH2:89]3)=[O:87])[CH3:85])[CH:79]=2)[CH2:74][CH2:73]1)=O)(C)(C)C>>[CH3:85][N:84]([C:80]1[CH:81]=[CH:82][CH:83]=[C:78]([N:75]2[CH2:74][CH2:73][NH:72][CH2:77][CH2:76]2)[CH:79]=1)[C:86]([N:88]1[C:92]2[N:93]=[C:94]([N:122]3[CH2:127][CH2:126][O:125][CH2:124][CH2:123]3)[N:95]=[C:96]([C:97]3[CH:98]=[N:99][C:100]([NH2:103])=[N:101][CH:102]=3)[C:91]=2[CH2:90][CH2:89]1)=[O:87]

Participants

4

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 592449624-{2-[Bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid (3-bromo-phenyl)-methyl-amideHCID 866401244-{3-[(4-{2-[Bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carbonyl)-methyl-amino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 592445544-(2-Amino-pyrimidin-5-yl)-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid methyl-(3-piperazin-1-yl-phenyl)-amideYield 78%

Procedure

Using 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 (3-bromo-phenyl)-methyl-amide (70.5 mg) and N-Boc-piperazine (34.9 mg) instead of 2-piperazin-1-yl-ethanol, in the same manner as Step C in Example 1-D-153, 4-{3-[(4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carbonyl)-methyl-amino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester was obtained as a crude product. Further, PMB group and BOC group were removed according to Deprotection method 3, to obtain the desired compound (D-154) as a yellow solid (37.9 mg, 78%).

Workup

  1. customFurther, PMB group and BOC group were removed

Sources & evidence

ORD record
ord-5eb0aa0aa7fb4872b7ab3d159629692e
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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