N-(2-((tert-butyldimethylsilyl)oxy)ethyl)propan-2-amine → HCID 178457470, compound

HRID 2169263Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10]([C:32](O)=[O:33])=[N:11][C:12]([CH2:16][C:17]2([C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:35]([O:42][CH2:43][CH2:44][NH:45][CH:46]([CH3:48])[CH3:47])([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36].[Si](OCCN(C(C)C)C(C1C(OCC2C=CC=CC=2)=C(O)N=C(CC2(C3C=C(Cl)C=CC=3Cl)CCCC2)N=1)=O)(C(C)(C)C)(C)C>>[Si:35]([O:42][CH2:43][CH2:44][N:45]([CH:46]([CH3:48])[CH3:47])[C:32]([C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:14]([OH:15])[N:13]=[C:12]([CH2:16][C:17]2([C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:11]=1)=[O:33])([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]

Participants

Reactant 3

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

HCID 178457482HCID 178457482, compound

HCID 178524862HCID 178524862, compound

Product 1

HCID 178457470HCID 178457470, compoundYield 24.5%

Procedure

5-Benzyloxy-6-hydroxy-2-(1-naphthalen-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (219) (300.0 mg, 24.5%) was synthesized as a colorless liquid from 5-benzyloxy-6-hydroxy-2-(1-naphthalen-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (218) (850.0 mg, 1.87 mmol) and [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropyl-amine (8b) (610.5 mg, 2.80 mmol) following the procedure described for 5-benzyloxy-2-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (206).

Sources & evidence

ORD record: ord-6f162a2ad32f4910a5c138893105fbbe
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045486B2

Reaction notes

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