HCID 59598570, compound → 5-(2-Isopropyl-4-methoxy-5-[1,2,4]oxadiazol-3-yl-phenoxy)-pyrimidine-2,4-diamine

HRID 1677325Notes

Reaction equation

HRID 1677325 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8]C=O)[C:5]([O:11][C:12]2[CH:17]=[C:16]([C:18]3[N:22]=[CH:21][O:20][N:19]=3)[C:15]([O:23][CH3:24])=[CH:14][C:13]=2[CH:25]([CH3:27])[CH3:26])=[CH:4][N:3]=1.NC1C(OC2C=C(C3N=CON=3)C(OC)=CC=2C(C)C)=CN=C(NC=O)N=1.C(NC1C(OC2C=C(C3N=CON=3)C(OC)=CC=2C(C)C)=CN=C(NC=O)N=1)=O>FC(F)(F)C(O)=O>[CH:25]([C:13]1[CH:14]=[C:15]([O:23][CH3:24])[C:16]([C:18]2[N:22]=[CH:21][O:20][N:19]=2)=[CH:17][C:12]=1[O:11][C:5]1[C:6]([NH2:8])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1)([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 59598570HCID 59598570, compoundHCID 59598574N-[4-formylamino-5-(2-isopropyl-4-methoxy-5-[1,2,4]oxadiazol-3-yl-phenoxy)-pyrimidin-2-yl]-formamideHCID 59598641N-[4-amino-5-(2-isopropyl-4-methoxy-5-[1,2,4]oxadiazol-3-yl-phenoxy)-pyrimidin-2-yl]formamide

Product 1

HCID 573296085-(2-Isopropyl-4-methoxy-5-[1,2,4]oxadiazol-3-yl-phenoxy)-pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of N-[2-amino-5-(2-isopropyl-4-methoxy-5-[1,2,4]oxadiazol-3-yl-phenoxy)-pyrimidin-4-yl]formamide, N-[4-amino-5-(2-isopropyl-4-methoxy-5-[1,2,4]oxadiazol-3-yl-phenoxy)-pyrimidin-2-yl]formamide and N-[4-formylamino-5-(2-isopropyl-4-methoxy-5-[1,2,4]oxadiazol-3-yl-phenoxy)-pyrimidin-2-yl]-formamide (0.164 g) in trifluoroacetic acid (10 mL) was heated at reflux for 24 h. The mixture was then cooled and concentrated in vacuo. The residue was purified by flash chromatography (0-5% methanol in dichloromethane) to yield 76 mg of 5-(2-isopropyl-4-methoxy-5-[1,2,4]oxadiazol-3-yl-phenoxy)-pyrimidine-2,4-diamine as its trifluoroacetic acid salt. (M+H)+=343; MP 135-138.5° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. temperatureThe mixture was then cooled
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (0-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-05f3f38c8d6e4ebf99e227d3aa9e8137
Source dataset
uspto-grants-2011_08
Patent number
US08008313B2

Reaction notes

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