Methyl iodide → 6-methyl-N2-(4-(oxazol-5-yl)phenyl)-N4-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine

HRID 1930539Notes

Reaction equation

HRID 1930539 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[O:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[N:21]=[C:22]([NH:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)C4CNCC[C:24]=4[N:25]=3)=[CH:15][CH:14]=2)=[CH:11][N:10]=[CH:9]1.IC>CN(C=O)C.O1CCOCC1>[CH3:1][N:3]1[CH2:6][CH2:7][C:24]2[N:25]=[C:20]([NH:19][C:16]3[CH:17]=[CH:18][C:13]([C:12]4[O:8][CH:9]=[N:10][CH:11]=4)=[CH:14][CH:15]=3)[N:21]=[C:22]([NH:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:5]=2[CH2:4]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 46200052N2-(4-(oxazol-5-yl)phenyl)-N4-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine

Product 1

HCID 462000536-methyl-N2-(4-(oxazol-5-yl)phenyl)-N4-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamineYield 23%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

Triethylamine (0.022 mL, 0.16 mmol) was added to N2-(4-(oxazol-5-yl)phenyl)-N4-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (0.06 g, 0.16 mmol, Example 3) in DMF (1 mL) and dioxane (1 mL). Iodomethane (0.031 g, 0.22 mmol) was added and the reaction stirred at 25° C. for 1 h. Solvent was removed under reduced pressure and the crude product redissolved in DMSO. The crude product was purified by preparative HPLC to give 6-methyl-N2-(4-(oxazol-5-yl)phenyl)-N4-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (0.014 g, 23%).

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe crude product redissolved in DMSO
  3. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-66d5a324b7574218a89dc5425853c33b
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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