3-Ethynyloxan-3-ol → 3-((1-(4-amino-1,3,5-triazin-2-yl)-2-methyl-1H-benzo[d]imidazol-6-yl)ethynyl)tetrahydro-2H-pyran-3-ol

HRID 1398698Notes

Reaction equation

HRID 1398698 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[C:12]3[CH:13]=[C:14]([C:17]#[C:18][C:19]4([OH:26])[CH2:24][CH:23]5C[CH:20]4C[CH2:22]5)[CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[CH3:27])[N:3]=1.C(C1(O)CCC[O:32]C1)#C>>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[C:12]3[CH:13]=[C:14]([C:17]#[C:18][C:19]4([OH:26])[CH2:24][CH2:23][CH2:22][O:32][CH2:20]4)[CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[CH3:27])[N:3]=1

Participants

3

Reactant 2

HCID 649161643-Ethynyloxan-3-olHCID 681817002-((1-(4-amino-1,3,5-triazin-2-yl)-2-methyl-1H-benzo[d]imidazol-6-yl)ethynyl)bicyclo[2.2.1]heptan-2-ol

Product 1

HCID 681816183-((1-(4-amino-1,3,5-triazin-2-yl)-2-methyl-1H-benzo[d]imidazol-6-yl)ethynyl)tetrahydro-2H-pyran-3-ol

Procedure

The title compound was prepared by the procedure described for 2-((1-(4-amino-1,3,5-triazin-2-yl)-2-methyl-1H-benzo[d]imidazol-6-yl)ethynyl)bicyclo[2.2.1]heptan-2-ol, by substituting 2-ethynylbicyclo [2.2.1]heptan-2-ol (1-b) with 3-ethynyltetrahydro-2H-pyran-3-ol. The title product, 3-((1-(4-amino-1,3,5-triazin-2-yl)-2-methyl-1H-benzo[d]imidazol-6-yl)ethynyl)tetrahydro-2H-pyran-3-ol was purified by silica gel chromatography: 1H NMR (400 MHz, DMSO) delta 1.66-1.78 (m, 4H), 1.97-2.05 (m, 1H), 3.01 (s, 3H), 3.36-3.71 (m, 4H), 7.47 (dd, J=1.6, 8.4 Hz, 1H), 7.71 (dd, J=0.4, 8.4 Hz, 1H), 8.17 (s, 1H), 8.24 (s, 1H), 8.48 (dd, J=0.4, 1.6 Hz, 1H), 8.71 (s, 1H); LC-MS: m/z=+350.9 (M+H)+.

Workup

  1. customThe title product, 3-((1-(4-amino-1,3,5-triazin-2-yl)-2-methyl-1H-benzo[d]imidazol-6-yl)ethynyl)tetrahydro-2H-pyran-3-ol was purified by silica gel chromatography

Sources & evidence

ORD record
ord-409c73fa0d034c5081009455ab750c8b
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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