Acetyl chloride → 1-[2,6-Dichloro-8-(3-chloro-4-fluorophenylamino)-4H-pyrimido[5,4-d]pyrimidin-3-yl]ethanone

HRID 23160Notes

Reaction equation

HRID 23160 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[CH:7]=[C:8]([NH:13][C:14]2[C:15]3[N:24]=[C:23]([Cl:25])[NH:22][CH2:21][C:16]=3[N:17]=[C:18]([Cl:20])[N:19]=2)[CH:9]=[CH:10][C:11]=1[F:12].C(N(C(C)C)C(C)C)C>C(OCC)(=O)C>[Cl:25][C:23]1[N:22]([C:1](=[O:3])[CH3:2])[CH2:21][C:16]2[N:17]=[C:18]([Cl:20])[N:19]=[C:14]([NH:13][C:8]3[CH:9]=[CH:10][C:11]([F:12])=[C:6]([Cl:5])[CH:7]=3)[C:15]=2[N:24]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 178505865HCID 178505865, compound

Product 1

HCID 225929701-[2,6-Dichloro-8-(3-chloro-4-fluorophenylamino)-4H-pyrimido[5,4-d]pyrimidin-3-yl]ethanone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

At 10° C., 56.4 ml (0.789 mol) of acetylchloride are added dropwise to a suspension of 210.6 g (0.608 mol) of (2) and 176 ml of N-ethyldiisopropylamine (0.95 mol) in 2.1 l of ethyl acetate. The mixture is stirred for 90 minutes at ambient temperature and then washed 3 times with 700 ml of water at 60° C. The organic phase is evaporated down and combined with 590 ml of ethanol. The mixture is briefly brought to boiling point, cooled to 0-5° C. and stirred at this temperature for 30 minutes. The product that crystallises out is filtered off and dried at 60° C. in vacuo. Yield: 180.3 g (76.3%), melting point: 177.6° C.

Workup

  1. washwashed 3 times with 700 ml of water at 60° C
  2. customThe organic phase is evaporated down
  3. temperaturecooled to 0-5° C.
  4. stirringstirred at this temperature for 30 minutes
  5. customThe product that crystallises out
  6. filtrationis filtered off
  7. customdried at 60° C. in vacuo

Sources & evidence

ORD record
ord-8058e984ccc84f6bafe07b67a366186a
Source dataset
uspto-grants-2005_02
Patent number
US06849734B2

Reaction notes

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