Tetrahydrofuran → 8-(4-Iodo-2-methoxy-pyridin-3-yl)-6-methyl-2-morpholin-4-yl-9H-purine

HRID 457555

Reaction equation

HRID 457555 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH:10]=[N:11][C:12]1[C:13]([NH2:25])=[N:14][C:15]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[N:16][C:17]=1[CH3:18].C1COCC1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>CO>[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[NH:25][C:13]2[C:12]([N:11]=1)=[C:17]([CH3:18])[N:16]=[C:15]([N:19]1[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1)[N:14]=2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 12217721Iodo benzene diacetateHCID 58819980N5-(4-Iodo-2-methoxy-pyridin-3-ylmethylene)-6-methyl-2-morpholin-4-yl-pyrimidine-4,5-diamine

Product 1

HCID 1784941868-(4-Iodo-2-methoxy-pyridin-3-yl)-6-methyl-2-morpholin-4-yl-9H-purineYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N5-(4-Iodo-2-methoxy-pyridin-3ylmethylene)-6-methyl-2-morpholin-4-yl-pyrimidine-4,5-diamine (140 mg, 0.31 mmol) in a mixture of MeOH:THF (20 mL: 10 mL) was added iodobenzene diacetate (198 mg, 0.62 mmol). After stirring at ambient temperature for 4 hours, the solvents were evaporated in vacuo and the crude was purified by preparative HPLC (see method below) to give the title compound as an amber solid (50 mg, 36%): IR (KBr, cm−1) 3420, 2853, 1618; 1H NMR (400 MHz, CDCl3) δ 9.63 (s, 1H), 7.83 and 7.54 (d, J=5.3, 1H), 3.91 (s, 3H), 3.81–3.77 (m, 8H), 2.72 (s, 3H); LCMS (+ESI, M+H+) m/z 453; HPLC: 97% (220 nm).

Workup

  1. customthe solvents were evaporated in vacuo
  2. customthe crude was purified by preparative HPLC (see method below)

Sources & evidence

ORD record
ord-3f6a966281734c0e8afd9d502cafa527
Source dataset
uspto-grants-2007_03
Patent number
US07189716B2

Linked notes

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