Dichloromethane → HCID 71283247, compound

HRID 1752431Notes

Reaction equation

HRID 1752431 reaction equation
[NH2:1][C:2](=[O:22])[C@@H:3]([NH:5][C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14](F)[CH:13]=2)[N:9]=[C:8]([C:19]([NH2:21])=[O:20])[CH:7]=1)[CH3:4].[F:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1.C([O-])([O-])=O.[Cs+].[Cs+].C(Cl)Cl>CN(C=O)C>[NH2:1][C:2](=[O:22])[C@@H:3]([NH:5][C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([O:30][C:27]3[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=3)[CH:13]=2)[N:9]=[C:8]([C:19]([NH2:21])=[O:20])[CH:7]=1)[CH3:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 71290072HCID 71290072, compound

Product 1

HCID 71283247HCID 71283247, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-(2-fluoropyridin-4-yl)pyrimidine-4-carboxamide (60 mg, 0.2 mmol), 4-fluorophenol (40 mg, 0.2 mmol) and Cs2CO3 (76 mg, 0.2 mmol) in DMF (1 mL) was placed in a microwave reaction vial and heated in a microwave oven at 160° C. for 20 minutes. The reaction was worked up with DCM then dried and evaporated. The residue was subjected to C18 flash chromatography using acetonitrile/H2O/0.1 TFA as the eluent and neutralized to give (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-(2-(4-fluorophenoxy)pyridin-4-yl)pyrimidine-4-carboxamide as white solid (40 mg, yield 50%). 1H NMR (CD3OD): 7.90-8.21 (3H, m), 6.90-7.2 (5H, m), 4.4 (1H, m), 1.35 (3H, d, J=7.0 Hz). LC/MS: m/z=398 [M+H]+.

Workup

  1. customwas placed in a microwave reaction vial
  2. customthen dried
  3. customevaporated

Sources & evidence

ORD record
ord-e47e15f34bb443d38e272627c34a9d16
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

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