2-(1-Naphthalen-2-yl-cyclopentyl)-acetamidine hydrochloride → HCID 178450802, compound

HRID 2169261Notes

Reaction equation

Cl.[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]1([CH2:17][C:18]([NH2:20])=[NH:19])[CH2:16][CH2:15][CH2:14][CH2:13]1.[C:21]([O:25][C:26]([C:28]1[C:33]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:32]([OH:42])N=C(CC2(C3C=C(Cl)C=CC=3Cl)CCCC2)N=1)=[O:27])([CH3:24])([CH3:23])[CH3:22]>>[C:21]([O:25][C:26]([C:28]1[C:33]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:32]([OH:42])[N:20]=[C:18]([CH2:17][C:12]2([C:3]3[CH:4]=[CH:5][C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH:2]=3)[CH2:16][CH2:15][CH2:14][CH2:13]2)[N:19]=1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

Reactant 2

HCID 867259112-(1-Naphthalen-2-yl-cyclopentyl)-acetamidine hydrochloride

HCID 178450815HCID 178450815, compound

Product 1

HCID 178450802HCID 178450802, compoundYield 45.2%

Procedure

5-Benzyloxy-6-hydroxy-2-(1-naphthalen-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (217) (4.0 g, 45.2%) was synthesized as a white solid from 2-(1-naphthalen-2-yl-cyclopentyl)-acetamidine hydrochloride (216) (5.0 g, 17.33 mmol) following the procedure described for 5-benzyloxy-2-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (204).

Sources & evidence

ORD record: ord-882f6272ee64433ba628e237a3672891
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045486B2

Reaction notes

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