Isopropyl iodide → 6-(3-fluorophenyl)-N-isopropylpyrido[3,2-d]pyrimidin-4-amine

HRID 1049911Notes

Reaction equation

HRID 1049911 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH2:18])[C:16]=3[N:17]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].I[CH:22]([CH3:24])[CH3:23]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH:18][CH:22]([CH3:24])[CH3:23])[C:16]=3[N:17]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 867039146-(3-Fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine

Product 1

HCID 867039136-(3-fluorophenyl)-N-isopropylpyrido[3,2-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(3-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine 1 (100 mg, 0.42 mmol) in DMF was treated with sodium hydride 60% dispersion in mineral oil (25 mg, 0.63 mmol) followed by 2-iodopropane (0.04 mL, 0.42 mmol), stirred at room temperature for 2 hrs. The reaction mixture was poured on ice, and extracted with EtOAc three times. The combined organic layers were dried with sodium sulfate and concentrated to dry. The crude was purified by ISCO eluting with 100% EtOAc to give pure 6-(3-fluorophenyl)-N-isopropylpyrido[3,2-d]pyrimidin-4-amine 25. LC/MS (ESI+): m/z 283 (M+H). 1H NMR (400 MHz, DMSO) δ 8.53-8.43 (m, 2H), 8.37 (d, J=10.8 Hz, 1H), 8.21 (t, J=8.4 Hz, 2H), 8.15 (d, J=8.8 Hz, 1H), 7.60 (dd, J=14.2, 8.0 Hz, 1H), 7.34 (td, J=8.5, 2.5 Hz, 1H), 4.56 (dq, J=13.3, 6.7 Hz, 1H), 1.35 (d, J=6.6 Hz, 6H).

Workup

  1. additionThe reaction mixture was poured on ice
  2. extractionextracted with EtOAc three times
  3. dry with materialThe combined organic layers were dried with sodium sulfate
  4. concentrationconcentrated
  5. customto dry
  6. customThe crude was purified by ISCO
  7. washeluting with 100% EtOAc

Sources & evidence

ORD record
ord-6a5b85cf8d1a4fa285e3dca673f85b70
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

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