Cesium carbonate → HCID 61279786, compound

HRID 1774161Notes

Reaction equation

HRID 1774161 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[O:15]1[CH2:20][CH2:19][CH:18]([NH2:21])[CH2:17][CH2:16]1>CN(C)C=O.C(OCC)(=O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:21][CH:18]2[CH2:19][CH2:20][O:15][CH2:16][CH2:17]2)[CH:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 709434,6-DichloropyrimidineHCID 4192234-Aminotetrahydropyran

Product 1

HCID 61279786HCID 61279786, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4,6-Dichloropyrimidine (3.06 g, 20.5 mmol) was dissolved in dimethylformamide (“DMF”) (20 mL) and Cs2CO3 (10.0 g, 30.8 mmol) was added. Tetrahydro-2H-pyran-4-amine (1.87 g, 18.5 mmol) combined with DMF (5 mL) was added dropwise. A slight exotherm was observed. After agitating at ambient temperature for 2 hours, product peak was seen in LC/MS. Agitation continued overnight. The mixture was then diluted with ethyl acetate (250 mL) and washed 4 times with water, brine, dried and evaporated to give 6-chloro-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine (2.86 g, 13.4 mmol, 65.2% yield) as a solid.

Workup

  1. additionwas added dropwise
  2. waitAgitation continued overnight
  3. washwashed 4 times with water, brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-f081151491694c0ead0c89aaf9b5a14e
Source dataset
uspto-grants-2016_02
Patent number
US09259470B2

Reaction notes

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