Dimethylformamide → Isobutyl 4-(6-chloropyrimidin-4-yl)piperazine-1-carboxylate

HRID 2266958Notes

Reaction equation

HRID 2266958 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[N:9]1([C:15]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(N(CC)CC)C.CN(C=O)C>O>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([N:12]2[CH2:11][CH2:10][N:9]([C:15]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[O:16])[CH2:14][CH2:13]2)[CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 709434,6-DichloropyrimidineHCID 11788701Isobutyl piperazine-1-carboxylate

Product 1

HCID 58857066Isobutyl 4-(6-chloropyrimidin-4-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4,6-dichloropyrimidine (0.25 g, 1.7 mmol), isobutyl piperazine-1-carboxylate (0.31 g, 1.7 mmol), triethylamine (0.23 mL, 1.8 mmol), and DMF (4.2 mL) was sealed in a microwave reactor vial and heated by microwave irradiation at 120° C. for 2 minutes. The reaction was cooled, diluted with water, and extracted with CH2Cl2. The combined extracts were dried over Na2SO4 and evaporated to obtain isobutyl 4-(6-chloropyrimidin-4-yl)piperazine-1-carboxylate. LC/MS: m/z 299.2 (M+H)+ at 3.10 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customwas sealed in a microwave reactor vial
  2. temperatureThe reaction was cooled
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-b76d7eebe7b245c98c3cc5ff70b1e57f
Source dataset
uspto-grants-2010_12
Patent number
US07858786B2

Reaction notes

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