2-Chlorobenzoyl chloride → HCID 86642733, compound

HRID 888979Notes

Reaction equation

HRID 888979 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[C:3]=1[NH2:16].[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>CC(N(C)C)=O>[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH:16][C:3]1[C:2]([Cl:1])=[N:7][C:6]([CH3:8])=[N:5][C:4]=1[NH:9][CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:21]

Participants

4

Reactant 2

HCID 691102-Chlorobenzoyl chlorideHCID 593745576-Chloro-2-methyl-N4-(tetrahydro-2H-pyran-4-yl)-4,5-pyrimidinediamine

Product 1

HCID 86642733HCID 86642733, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
2.5 °C

Procedure

Dissolve 6-chloro-2-methyl-N*4*-(tetrahydro-2H-pyran-4-yl)-pyrimidine-4,5-diamine (24.4 g, 100.4 mmol) in dimethylacetamide (175 mL) in a 500 mL 3-necked flask under a nitrogen atmosphere. Cool the resulting solution to 0-5° C. Via addition funnel, add 2-chlorobenzoyl chloride (15.5 mL, 122.4 mmol) over 20 minutes, maintaining the internal temperature below 10° C. Rinse the addition funnel with dimethylacetamide (1.0 mL). Allow the resulting mixture to stir overnight while self-warming to ambient temperature. Charge ice cold de-ionized water (250 mL) to a second 500 mL flask and then transfer the reaction mixture into the cold water over 20 minutes. Stir the resulting slurry for 2 hours. Filter the solids, wash with cold water (120 mL)) and vacuum dry overnight at 50° C. to afford 2-chloro-N-(4-chloro-2-methyl-6-(tetrahydro-2H-pyran-4-ylamino)-pyrimidin-5-yl) benzamide as an off-white solid (33.1 g). MS (m/z): 381/382 (M+1).

Workup

  1. additionVia addition funnel
  2. temperaturemaintaining the internal temperature below 10° C
  3. washRinse the addition funnel with dimethylacetamide (1.0 mL)
  4. temperaturewhile self-warming to ambient temperature
  5. customCharge ice cold de-ionized water (250 mL) to a second 500 mL flask and then transfer
  6. waitthe reaction mixture into the cold water over 20 minutes
  7. stirringStir the resulting slurry for 2 hours
  8. filtrationFilter the solids
  9. washwash with cold water (120 mL)) and vacuum
  10. customdry overnight at 50° C.

Sources & evidence

ORD record
ord-b18bdc730d164ad995591c8b8a7792bd
Source dataset
uspto-grants-2012_08
Patent number
US08252798B2

Reaction notes

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