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

HRID 2266153Notes

Reaction equation

HRID 2266153 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-6026227b4c014f92b0f192ade3930db6
Source dataset
uspto-grants-2010_12
Patent number
US07858632B2

Reaction notes

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