4-Amino-3-chlorophenol → 4-amino-6-(4-amino-3-chloro-phenoxy)-pyrimidine-5-carbaldehyde O-methyl-oxime

HRID 907434Notes

Reaction equation

HRID 907434 reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[C:6]([NH2:12])=[N:7][CH:8]=[N:9][C:10]=1Cl.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=1[Cl:21]>>[CH3:1][O:2][N:3]=[CH:4][C:5]1[C:6]([NH2:12])=[N:7][CH:8]=[N:9][C:10]=1[O:20][C:17]1[CH:18]=[CH:19][C:14]([NH2:13])=[C:15]([Cl:21])[CH:16]=1

Participants

3

Reactant 2

HCID 871844-Amino-3-chlorophenolHCID 724866374-amino-6-chloro-pyrimidine-5-carbaldehyde O-methyl-oxime

Product 1

HCID 724866124-amino-6-(4-amino-3-chloro-phenoxy)-pyrimidine-5-carbaldehyde O-methyl-oxime

Procedure

Using the procedure for Example 9, 4-amino-6-chloro-pyrimidine-5-carbaldehyde O-methyl-oxime Compound 9a (0.20 g) and 4-amino-3-chloro-phenol Compound 10a (0.19 g) were reacted to provide 4-amino-6-(4-amino-3-chloro-phenoxy)-pyrimidine-5-carbaldehyde O-methyl-oxime Compound 10b (0.20 g, 65%). 1H NMR (400 MHz, DMSO-d6) δ 8.55 (s, 1H), 8.15 (s, 1H), 8.05 (s, 1H), 7.60 (s, 1H), 7.15 (s, 1H), 6.90 (d, 1H), 6.80 (d, 1H), 5.32 (s, 2H), 3.98 (s, 3H). MS (ESI) m/z: 299 (M+H+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-55a5aa11502f4708a93f92ef9df08a44
Source dataset
uspto-grants-2011_09
Patent number
US08013153B2

Reaction notes

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