Methyl iodide → 2-(1,1-Dioxo-1lambda6-thiomorpholin-4-yl)-7-methyl-4-p-tolyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine

HRID 72807Notes

Reaction equation

HRID 72807 reaction equation
[O:1]=[S:2]1(=[O:26])[CH2:7][CH2:6][N:5]([C:8]2[N:9]=[C:10]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[C:11]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13][C:12]=3[N:18]=2)[CH2:4][CH2:3]1.IC.[CH2:29](N(C(C)C)C(C)C)C>C(Cl)Cl>[O:26]=[S:2]1(=[O:1])[CH2:3][CH2:4][N:5]([C:8]2[N:9]=[C:10]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[C:11]3[CH2:17][CH2:16][N:15]([CH3:29])[CH2:14][CH2:13][C:12]=3[N:18]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 46202640HCID 46202640, compound

Product 1

HCID 462026412-(1,1-Dioxo-1lambda6-thiomorpholin-4-yl)-7-methyl-4-p-tolyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepineYield 16.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-(1,1-dioxo-1λ6-thiomorpholin-4-yl)-4-p-tolyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine (0.060 g, 0.00016 mol), iodomethane (0.015 mL, 0.00016 mol) and N-ethyl-N-(1-methylethyl)-2-propanamine (0.056 mL, 0.00032 mol) in DCM (2 mL) was stirred at rt for 3 h. The mixture was diluted with DCM and washed with water (3×) and satd. aq. NaCl. The separated organic layer was dried and concentrated. The residue was purified by FCC [7 N NH3/MeOH)/DCM] to give 0.010 g (16%) of the title compound.

Workup

  1. washwashed with water (3×)
  2. customThe separated organic layer was dried
  3. concentrationconcentrated
  4. customThe residue was purified by FCC [7 N NH3/MeOH)/DCM]

Sources & evidence

ORD record
ord-e990197c8c5d464686f8c1b6b62ba4cd
Source dataset
uspto-grants-2014_09
Patent number
US08829011B2

Reaction notes

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