Ethyl Acetate → HCID 86626630, compound

HRID 556372Notes

Reaction equation

HRID 556372 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]2[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:9]=12)=[O:4].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[NH2:23][C:24]1[N:29]=[C:28](Cl)[CH:27]=[C:26]([Cl:31])[N:25]=1.CCOC(C)=O>CN1C(=O)CCC1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]2[CH:13]=[C:12]([O:14][C:28]3[CH:27]=[C:26]([Cl:31])[N:25]=[C:24]([NH2:23])[N:29]=3)[CH:11]=[CH:10][C:9]=12)=[O:4]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 655222-Amino-4,6-dichloropyrimidineHCID 66992907HCID 66992907, compound

Product 1

HCID 86626630HCID 86626630, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
70 °C

Procedure

58.9 mg Product from Step 15.6 (0.31 mMol) are dissolved in 8 ml NMP and treated with 268 mg (1.2 mMol) K3PO4 and 75 mg (0.46 mMol) 2-amino-4,6-dichloropyrimidine at rt. The reaction mixture is warmed to 70° C. and stirred for 20 h at rt. It is worked up by addition of EtOAc and washed with H2O. The organic layer is dried and concentrated to give the crude product which is purified by recrystallization from EtOAc to give the title compound as a white powder: MS: [M+1]+=320; 1H MNR (DMSO-d6): δ ppm 9.18 (s, 1H), 8.43 (s, 1H), 8.09 (d, 1H), 7.60 (d, 1H), 7.21 (bs, 2H, NH2), 6.42 (s, 1H), 3.82 (s, 3H).

Workup

  1. washwashed with H2O
  2. customThe organic layer is dried
  3. concentrationconcentrated
  4. customto give the crude product which
  5. customis purified by recrystallization from EtOAc

Sources & evidence

ORD record
ord-820bb0a5a0da47048848c8537772e5f8
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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