Ethanol → HCID 18768043, compound

HRID 480021Notes

Reaction equation

HRID 480021 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[NH:9]([C:16]1[C:21]([Br:22])=[CH:20][N:19]=[C:18]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=2)[N:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O)C>O>[NH2:30][C:27]1[CH:28]=[CH:29][C:24]([NH:23][C:18]2[N:17]=[C:16]([NH:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:21]([Br:22])=[CH:20][N:19]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24489Sodium DithioniteHCID 18768056HCID 18768056, compound

Product 1

HCID 18768043HCID 18768043, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydrosulphite (9.5 g, 54.5 mmol) was added over 30 minutes to a stirred solution of anilino-5-bromo-2-(4-nitroanilino)pyrimidine (Method 39; 7.0 g, 18.2 mmol) in a hot mixture of ethanol and water (1:1, 100 ml). The resulting suspension was stirred for a further two hours and insoluble material was removed by filtration. The filtrate was concentrated and the residue was partitioned between 1M aqueous sodium hydroxide (50 ml), and DCM (100 ml). The organic layer was separated, washed with water (2×10 ml) and dried. Volatile material was removed by evaporation to give the product (4.55 g, 70%). MS (MH+): 356, 358.

Workup

  1. custominsoluble material was removed by filtration
  2. concentrationThe filtrate was concentrated
  3. customthe residue was partitioned between 1M aqueous sodium hydroxide (50 ml), and DCM (100 ml)
  4. customThe organic layer was separated
  5. washwashed with water (2×10 ml)
  6. customdried
  7. customVolatile material was removed by evaporation

Sources & evidence

ORD record
ord-41e7102dc5f44e05bd0fd4c31727f8ae
Source dataset
uspto-grants-2003_11
Patent number
US06649608B2

Reaction notes

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