2,4-Dichloro-5-fluoropyrimidine → HCID 178434337, compound

HRID 1640702Notes

Reaction equation

HRID 1640702 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[NH:4][N:3]=1.C([O-])(O)=O.[Na+].[F:17][C:18]1[C:19](Cl)=[N:20][C:21]([Cl:24])=[N:22][CH:23]=1>C1COCC1.CCO>[Cl:24][C:21]1[N:22]=[C:23]([NH:11][C:7]2[CH:6]=[C:5]3[C:10]([C:2]([CH3:1])=[N:3][NH:4]3)=[CH:9][CH:8]=2)[C:18]([F:17])=[CH:19][N:20]=1

Participants

6

Reactant 3

HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 516892Sodium BicarbonateHCID 178434350HCID 178434350, compound

Product 1

HCID 178434337HCID 178434337, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-methyl-6-aminoindazole (2.71 g, 0.015 mol) and NaHCO3 (1.26 g, 0.045 mol) in THF (15 mL) and EtOH (60 mL) was added 5-fluoro-2,4-dichloropyrimidine (3.2 g, 0.019 mol) at room temperature. After the reaction was stirred overnight, the brown suspension was filtered and washed thoroughly with EtOH. The filtrate was concentrated under reduced pressure, and the resulting solid was washed with ether to remove excess pyrimidine to yield 3.7 g of the desired product (89%). HNMR: δ 12.57 (s, 1H), 10.01 (s, 1H), 8.28 (d, 1H), 7.93 (s, 1H), 7.60 (d, 1H), 7.27 (dd, 1H) 3.11 (s, 3H).

Workup

  1. filtrationthe brown suspension was filtered
  2. washwashed thoroughly with EtOH
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. washthe resulting solid was washed with ether
  5. customto remove excess pyrimidine

Sources & evidence

ORD record
ord-f6bd8fd06d3e4982951fbfd2223baaa2
Source dataset
uspto-grants-2012_02
Patent number
US08114885B2

Reaction notes

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