Sodium Hydroxide → HCID 9891821, compound

HRID 1384064Notes

Reaction equation

HRID 1384064 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 1N 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-b2e871c1d9e1472e91ffe00fe52403cb
Source dataset
uspto-grants-2001_07
Patent number
US06258809B1

Reaction notes

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