Sodium Hydroxide → HCID 9891821, compound

HRID 1954839Notes

Reaction equation

HRID 1954839 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:27]([CH3:30])([CH3:29])[OH:28])[CH:5]=[C:6]([O:25][CH3:26])[C:7]=1[O:8][C:9]1[C:14]([NH2:15])=[C:13]([NH:16][CH:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[N:12]=[C:11]([CH3:24])[N:10]=1.[N:31]([O-])=O.[Na+].[OH-].[Na+]>C(O)(=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([C:27]([CH3:30])([CH3:29])[OH:28])[CH:5]=[C:6]([O:25][CH3:26])[C:7]=1[O:8][C:9]1[C:14]2[N:15]=[N:31][N:16]([CH:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[C:13]=2[N:12]=[C:11]([CH3:24])[N:10]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 15548996HCID 15548996, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 9891821HCID 9891821, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of 3-bromo-5-methoxy-α,α-dimethyl-4-[[5-amino-2-methyl-6-[(1-propylbutyl)amino]-4-pyrimidinyl]oxy]benzene-methanol (0.70 g) in 35 mL of glacial acetic acid, 0.10 g of sodium nitrite in 1 mL of water was added dropwise. The mixture was stirred at room temperature for 20 minutes and then diluted with water, basified with 1 N NaOH and extracted three times with ethyl acetate. The combined extracts were dried over MgSO4 and stripped of the solvent under reduced pressure to yield the title compound as viscous liquid.

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined extracts were dried over MgSO4

Sources & evidence

ORD record
ord-2ee070c7dd7740308ba113322edc2917
Source dataset
uspto-grants-2000_09
Patent number
US06124300

Reaction notes

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