6-Chloro-N-[4-(methanesulfonyl)phenyl]-5-nitropyrimidin-4-amine → HCID 21897803, compound

HRID 1864165Notes

Reaction equation

HRID 1864165 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[C:3]=1[N+:19]([O-])=O.[N:22]([O-])=O.[Na+]>ClCCl.C(O)(=O)C.O>[Cl:1][C:2]1[C:3]2[N:19]=[N:22][N:8]([C:9]3[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 2

HCID 218978866-Chloro-N-[4-(methanesulfonyl)phenyl]-5-nitropyrimidin-4-amineHCID 23668193Sodium Nitrite

Product 1

HCID 21897803HCID 21897803, compoundYield 77.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-chloro-5-nitro-pyrimidin-4-yl)-(4-methanesulfonyl-phenyl)-amine in dichloromethane (8 mL) and 50% aqueous acetic acid (6 mL) was added sodium nitrite (64.6 mg, 0.937 mmol) in water (1 mL) dropwise at room temperature. After the addition was complete, the reaction was stirred for additional 15 minutes at room temperature. The organic layer was then separated, washed with water, and dried over anhydrous magnesium sulfate. Filtration followed by removal of volatiles under high vacuum afforded the desired product as a yellow solid (205 mg, 77.8%).

Workup

  1. additionAfter the addition
  2. customThe organic layer was then separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationFiltration
  6. customfollowed by removal of volatiles under high vacuum

Sources & evidence

ORD record
ord-e2bc7bec49fa4f6fad06b8607b6f83bd
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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