Dimethylformamide → 2-chloro-N-(2,2,2-trifluoroethyl)furo[3,2-d]pyrimidin-4-amine

HRID 1038861Notes

Reaction equation

HRID 1038861 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1.CN(C=O)C.[F:17][C:18]([F:22])([F:21])[CH2:19][NH2:20]>CCOCC>[Cl:1][C:2]1[N:3]=[C:4]([NH:20][CH2:19][C:18]([F:22])([F:21])[F:17])[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 457899682,4-Dichlorofuro[3,2-D]pyrimidine

Product 1

HCID 866651142-chloro-N-(2,2,2-trifluoroethyl)furo[3,2-d]pyrimidin-4-amineYield 71.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

To a flask was added 2,4-dichlorofuro[3,2-d]pyrimidine (0.80 g, 4.23 mmol, ArkPharm) and DMF (3.0 mL). 2,2,2-Trifluoroethanamine (1.05 g, 10.58 mmol, Acros) was added. The mixture was heated in a microwave at about 120° C. for about 15 min. The mixture was diluted with Et2O (100 mL). The mixture was washed with water (3×25 mL). The combined aqueous layer was extracted with Et2O (2×50 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was transferred neat and was purified by preparative TLC eluting with 3:1 hexanes/EtOAc to give 2-chloro-N-(2,2,2-trifluoroethyl)furo[3,2-d]pyrimidin-4-amine (0.76 g, 71%): LC/MS (Table 2, Method h) Rt=1.85 min; MS m/z: 252, 254 (M+H)+.

Workup

  1. washThe mixture was washed with water (3×25 mL)
  2. extractionThe combined aqueous layer was extracted with Et2O (2×50 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customwas purified by preparative TLC
  7. washeluting with 3:1 hexanes/EtOAc

Sources & evidence

ORD record
ord-45923308fb074e478736225c7ad81d08
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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