2-(2-Bromophenyl)ethanimidamide hydrochloride → HCID 178450816, compound

HRID 2169222Notes

Reaction equation

HRID 2169222 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([NH2:12])=[NH:11].C[O:14][C:15](=O)/[C:16](/[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[C:17](\O)/[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C(OC(C1C(OCC2C=CC=CC=2)=C(O)N=C(CC2C=CC=C(Cl)C=2Cl)N=1)=O)(C)(C)C>>[C:21]([O:20][C:18]([C:17]1[C:16]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:15]([OH:14])[N:12]=[C:10]([CH2:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[Br:2])[N:11]=1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 3

HCID 145311952-(2-Bromophenyl)ethanimidamide hydrochlorideHCID 546790054-Tert-butyl 1-methyl 2-(benzyloxy)-3-hydroxyfumarateHCID 178450819HCID 178450819, compound

Product 1

HCID 178450816HCID 178450816, compoundYield 83.3%

Procedure

5-Benzyloxy-2-(2-bromobenzyl)-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (148) (28 g, crude) as a brown solid was synthesized from 2-(2-bromophenyl)-acetamidine hydrochloride salt (147) (17.76 g, 71.32 mmol) and (E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester 1-methyl ester (4) (32.95 g, 106.98 mmol) following the procedure as described for 5-benzyloxy-2-(2,3-dichlorobenzyl)-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (130). The product was used without purification for further synthesis.

Workup

  1. customThe product was used without purification for further synthesis

Sources & evidence

ORD record
ord-5ef5a47557e84aaeac62512506c6dce9
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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