Methanol → 5-(2-Chloro-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one

HRID 1770776Notes

Reaction equation

HRID 1770776 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.[Cl:12][C:13]1[N:18]=[C:17](Cl)[C:16]([CH3:20])=[CH:15][N:14]=1.CO>O>[Cl:12][C:13]1[N:18]=[C:17]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[O:9][C:8](=[O:10])[NH:7][C:6]=3[CH:11]=2)[C:16]([CH3:20])=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 268565-Amino-2,3-dihydro-1,3-benzoxazol-2-oneHCID 74508Pyrimidine, 2,4-dichloro-5-methyl-

Product 1

HCID 580713875-(2-Chloro-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-oneYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a vial with 5-aminobenzo[d]oxazol-2(3H)-one (300.1 mg, 2.0 mmol) and 2,4-dichloro-5-methylpyrimidine (423.8 mg, 2.6 mmol), MeOH (8 mL) and H2O (2 mL) were added. The turbid mixture was stirred at room temperature for 64 h. Precipitate from reaction mixture was collected by filtration, washing with EtOAc (3 mL×2), and was further dried in vacuo. 5-(2-Chloro-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one was obtained as an off-white solid: 394 mg (71% yield); 1H NMR (300 MHz, DMSO) δ 11.68 (br s, 1H), 8.62 (s, 1H), 7.94 (d, J=0.8, 1H), 6.97 (d, J=2.0, 1H), 6.82 (d, J=8.1, 1H), 6.74 (dd, J=2.0, 8.1, 1H), 2.15 (s, 3H); LCMS (M+) m/z 277.10.

Workup

  1. customPrecipitate from reaction mixture
  2. filtrationwas collected by filtration
  3. washwashing with EtOAc (3 mL×2)
  4. customwas further dried in vacuo

Sources & evidence

ORD record
ord-4cb03ba899954dfcbca335292a13b68a
Source dataset
uspto-grants-2016_02
Patent number
US09248132B2

Reaction notes

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