3-Fluorobenzoyl chloride → HCID 22597419, compound

HRID 1760214Notes

Reaction equation

HRID 1760214 reaction equation
[NH2:1][C:2]1[C:3]([NH:9][C:10]2[CH:11]=[CH:12][C:13](=[O:17])[N:14]([CH3:16])[CH:15]=2)=[N:4][CH:5]=[N:6][C:7]=1[Cl:8].[F:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22](Cl)=O.C(=O)(O)[O-].[Na+].NC1N=CN=C2C=1N=C(C1C=CC=C(F)C=1)N2C1C=CC(=O)N(C)C=1>C(OCC)(=O)C.CN1C(=O)CCC1>[Cl:8][C:7]1[N:6]=[CH:5][N:4]=[C:3]2[C:2]=1[N:1]=[C:22]([C:21]1[CH:25]=[CH:26][CH:27]=[C:19]([F:18])[CH:20]=1)[N:9]2[C:10]1[CH:11]=[CH:12][C:13](=[O:17])[N:14]([CH3:16])[CH:15]=1

Participants

7

Reactant 4

HCID 743763-Fluorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 9949620HCID 9949620, compoundHCID 225974245-[(5-Amino-6-chloro-4-pyrimidinyl)amino]-1-methyl-2(1H)-pyridinone

Product 1

HCID 22597419HCID 22597419, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
40 °C

Procedure

5-(5-Amino-6-chloropyrimidin-4-yl)amino-1-methyl-1,2-dihydro-2-pyridinone (1 g) and NMP (10 mL) were introduced into a flask and stirred at 40° C. 3-Fluorobenzoyl chloride (0.53 mL, 1.1 eq.) was added dropwise to this suspension, and after additional NMP (3.2 mL) was added thereto and stirred for about 1.5 hours, the reaction solution was elevated to 110° C. and stirred for 3 hours. Ethyl acetate (33 mL) and 10% aqueous sodiumbicarbonate solution (16.5 mL) were added to the reaction solution, and the organic layer was washed with brine (16.5 mL) and concentrated. The concentrate was dissolved by adding DME (16.5 mL) and stirring it at 55° C., and then crystallized by adding water (33 mL). The crystals were collected by filtration and dried at 50° C. for 4 hours, to give 0.94 g of 5-[6-chloro-8-(3-fluorophenyl)-9H-9-purinyl]-1-methyl-1,2-dihydro-2-pyridinone (two-steps, yield 66.7%) (6) 5-[6-Amino-8-(3-fluorophenyl)-9H-9-purinyl]-1-methyl-1,2-dihydro-2-pyridinone

Workup

  1. stirringstirred for about 1.5 hours
  2. customwas elevated to 110° C.
  3. stirringstirred for 3 hours
  4. washthe organic layer was washed with brine (16.5 mL)
  5. concentrationconcentrated
  6. dissolutionThe concentrate was dissolved
  7. additionby adding DME (16.5 mL)
  8. stirringstirring it at 55° C.
  9. customcrystallized
  10. additionby adding water (33 mL)
  11. filtrationThe crystals were collected by filtration
  12. customdried at 50° C. for 4 hours

Sources & evidence

ORD record
ord-bbad37e6173741299936f10f754e8c44
Source dataset
uspto-grants-2005_01
Patent number
US06841549B1

Reaction notes

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