Cesium carbonate → 6-(6-chloro-2-cyclopropylpyrimidin-4-yloxy)-4-methylbenzo[d]oxazol-2(3H)-one

HRID 1846472Notes

Reaction equation

HRID 1846472 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([CH:9]2[CH2:11][CH2:10]2)[N:3]=1.[OH:12][C:13]1[CH:22]=[C:21]([CH3:23])[C:16]2[NH:17][C:18](=[O:20])[O:19][C:15]=2[CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:8][C:6]1[N:5]=[C:4]([CH:9]2[CH2:11][CH2:10]2)[N:3]=[C:2]([O:12][C:13]2[CH:22]=[C:21]([CH3:23])[C:16]3[NH:17][C:18](=[O:20])[O:19][C:15]=3[CH:14]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 249036874,6-Dichloro-2-cyclopropylpyrimidineHCID 669780936-hydroxy-4-methylbenzo[d]oxazol-2(3H)-one

Product 1

HCID 866639166-(6-chloro-2-cyclopropylpyrimidin-4-yloxy)-4-methylbenzo[d]oxazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.10 g (0.53 mmol) 4,6-dichloro-2-cyclopropylpyrimidine were added to 95 mg (0.55 mmol) 6-hydroxy-4-methylbenzo[d]oxazol-2(3H)-one and 0.21 g (0.63 mmol) caesium carbonate in 1.5 mL DMF after 15 min and the mixture was stirred overnight at RT. The reaction mixture was purified by preparative HPLC-MS. The fractions containing product were combined and freeze-dried.

Workup

  1. customThe reaction mixture was purified by preparative HPLC-MS
  2. additionThe fractions containing product
  3. customfreeze-dried

Sources & evidence

ORD record
ord-c23107c4d3344f59aa73be9c16e36e58
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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