N-(2-((tert-butyldimethylsilyl)oxy)ethyl)propan-2-amine → HCID 178457487, compound

HRID 2169440Notes

Reaction equation

[Si](OCCN(C)C(C1C(OCC2C=CC=CC=2)=C(O)N=C(CC2(N3C4=NC=CC=C4C=C3)CCCC2)N=1)=O)(C(C)(C)C)(C)C.[CH2:45]([O:52][C:53]1[C:54]([C:75](O)=[O:76])=[N:55][C:56]([CH2:60][C:61]2([N:66]3[C:70]4=[N:71][CH:72]=[CH:73][CH:74]=[C:69]4[CH:68]=[CH:67]3)[CH2:65][CH2:64][CH2:63][CH2:62]2)=[N:57][C:58]=1[OH:59])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.[Si:78]([O:85][CH2:86][CH2:87][NH:88][CH:89]([CH3:91])[CH3:90])([C:81]([CH3:84])([CH3:83])[CH3:82])([CH3:80])[CH3:79]>>[Si:78]([O:85][CH2:86][CH2:87][N:88]([CH:89]([CH3:91])[CH3:90])[C:75]([C:54]1[C:53]([O:52][CH2:45][C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)=[C:58]([OH:59])[N:57]=[C:56]([CH2:60][C:61]2([N:66]3[C:70]4=[N:71][CH:72]=[CH:73][CH:74]=[C:69]4[CH:68]=[CH:67]3)[CH2:62][CH2:63][CH2:64][CH2:65]2)[N:55]=1)=[O:76])([C:81]([CH3:84])([CH3:83])[CH3:82])([CH3:80])[CH3:79]

Participants

Reactant 3

HCID 57917054N-(2-((tert-butyldimethylsilyl)oxy)ethyl)propan-2-amine

HCID 178484774HCID 178484774, compound

HCID 178524881HCID 178524881, compound

Product 1

HCID 178457487HCID 178457487, compound

Procedure

5-Benzyloxy-6-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (409) was prepared following the same method as described for 5-benzyloxy-6-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-methyl-amide (405) from 5-benzyloxy-6-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (404) (250 mg, 0.56 mmol) and [2-(tert-tutyl-dimethylsilanyloxy)-ethyl]-isopropyl-amine (367 mg, 1.69 mmol) (8b) to get an off-white sticky solid (220 mg, 61%).

Sources & evidence

ORD record: ord-f930608c51dc4a388d93330b41aadab5
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045486B2

Reaction notes

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