Dichloromethane → HCID 9928255, compound

HRID 2305991Notes

Reaction equation

HRID 2305991 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[N:14]=[C:13]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[C:12]([O:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[CH:11][N:10]=1.C(N(CC)CC)C.ClCCl>O1CCCC1>[C:1]([N:18]1[CH2:17][CH2:16][N:15]([C:13]2[C:12]([O:21][C:22]3[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=3)=[CH:11][N:10]=[C:9]([NH2:8])[N:14]=2)[CH2:20][CH2:19]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 9861322HCID 9861322, compound

Product 1

HCID 9928255HCID 9928255, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Acetic anhydride (Aldrich) (0.318 g, 3.11 mmoles) in tetrahydrofuran (1.5 mL) was added to a solution of 2-amino-5-(4-chlorophenoxy)-4-(piperazino)pyrimidine (0.511 g, 1.67 mmoles) and triethylamine (0.526 g, 5.20 mmoles) in tetrahydrofuran (13 mL). After 0.5 hours the solution was diluted with ice water (40 mL) and poured into dichloromethane (75 mL). The layers were separated, and the organic layer was washed with saturated aqueous sodium bicarbonate (40 mL), brine (40 mL) and then dried over sodium sulfate. The dry solution was spin evaporated in vacuo to give a white foam. The foam was recrystallized from hexanes-ethyl acetate to give 0.348 g (60% yield) of 4-(4-acetylpiperazino)-2-amino-5-(4-chlorophenoxy)pyrimidine as beige pins, mp 153-157° C.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with saturated aqueous sodium bicarbonate (40 mL), brine (40 mL)
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customto give a white foam
  6. customThe foam was recrystallized from hexanes-ethyl acetate

Sources & evidence

ORD record
ord-3a537766a0804f738dd03006f4dab744
Source dataset
uspto-grants-2002_08
Patent number
US06440965B1

Reaction notes

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