5-Bromo-o-toluidine → 3'-Amino-4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-4'-methyl-biphenyl-2-ol

HRID 2416324Notes

Reaction equation

HRID 2416324 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:16]=[C:17]([O:20]COC)[C:18]=1I)[CH2:7][C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1)[CH3:2].Br[C:25]1[CH:26]=[CH:27][C:28]([CH3:38])=[C:29]([NH:31]C(=O)C(F)(F)F)[CH:30]=1.BrC1C=CC(C)=C(C=1)N>>[NH2:31][C:29]1[CH:30]=[C:25]([C:18]2[C:17]([OH:20])=[CH:16][C:6]([CH2:7][C:8]3[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=3)=[CH:5][C:4]=2[O:3][CH2:1][CH3:2])[CH:26]=[CH:27][C:28]=1[CH3:38]

Participants

4

Reactant 3

HCID 27348055-Bromo-o-toluidineHCID 22636933HCID 22636933, compoundHCID 22637059N-(5-bromo-2-methylphenyl)-2,2,2-trifluoroacetamide

Product 1

HCID 226370073'-Amino-4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-4'-methyl-biphenyl-2-olYield 30%

Procedure

Starting from 5-(3-ethoxy-4-iodo-5-methoxymethoxy-benzyl)-pyrimidine-2,4-diamine (2.11 g; 4,9 mmol) and N-(5-bromo-2-methyl-phenyl)-2,2,2-trifluoro-acetamide (prepared from 5-bromo-2-methyl-aniline analogously to example 41) (2.3 g; 8.17 mmol), 0.963 g (30%) 3′-amino-4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-4′-methyl-biphenyl-2-ol is obtained as a beige powder after Suzuki coupling (in situ generation of R2—B(OH)2) and splitting off of the protective group under acid conditions.

Sources & evidence

ORD record
ord-8c1a99884cdc4c508e9146373bb314a4
Source dataset
uspto-grants-2004_11
Patent number
US06821980B1

Reaction notes

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