Water → HCID 86762310, compound

HRID 2362190Notes

Reaction equation

HRID 2362190 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9][CH2:8][C:6]=2[N:7]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][CH2:27][NH2:28].CCOC(C)=O.O>CN(C=O)C>[C:15]([O:14][C:12]([N:10]1[CH2:9][CH2:8][C:6]2[N:7]=[C:2]([Cl:1])[N:3]=[C:4]([NH:28][CH2:27][CH2:26][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=3)[C:5]=2[CH2:11]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 759192-PyridineethanamineHCID 17998716tert-Butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Product 1

HCID 86762310HCID 86762310, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (100 mg, 0.329 mmol) and TEA (0.137 mL, 0.986 mmol) in DMF (1.5 mL) was treated with 2-(2-pyridyl)ethyl amine (40.2 mg, 0.329 mmol). The mixture was stirred overnight at room temperature. The reaction mixture was EtOAc (10 mL) and H2O (10 mL), and extracted with EtOAc (2×10 mL). The combined organic phases were washed with H2O (10 mL) and brine (10 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue was purified by gradient elution on silica gel (0 to 100% EtOAc in hexanes to afford the title compound as a pale yellow gum (96 mg, 75%). Data for G-1: 1H NMR (500 MHz, CDCl3) δ 8.524-8.64 (br m, 1H), 7.61-7.69 (br m, 1H), 7.15-7.24 (m, 2H), 6.67-6.89 (br m, 1H), 4.24 (s, 2H), 3.67 (br m, 2H), 3.08 (t, J=9.0 Hz, 2H), 2.75 (br s, 2H), 1.51 (s, 9H); LC/MS: rt=1.35 min, m/z (M+H)=390.1 found; 390.2 calcd.

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. washThe combined organic phases were washed with H2O (10 mL) and brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by gradient elution on silica gel (0 to 100% EtOAc in hexanes

Sources & evidence

ORD record
ord-09cb2f241ffe4712853b60587ce0a25a
Source dataset
uspto-grants-2014_04
Patent number
US08691827B2

Reaction notes

Loading…