HCID 67329355, compound → HCID 53373128, compound

HRID 1846197Notes

Reaction equation

HRID 1846197 reaction equation
[CH3:1][N:2]([CH3:26])[C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6]([OH:11])=[C:5]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22]COC)[N:4]=1>CO.Cl>[CH3:26][N:2]([CH3:1])[C:3]1[N:4]=[C:5]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])[C:6]([OH:11])=[C:7]([O:9][CH3:10])[N:8]=1

Participants

4

Reactant 1

HCID 67329355HCID 67329355, compound

Product 1

HCID 53373128HCID 53373128, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution containing 20 mg (0.054 mmol) of 2-(dimethylamino)-4-methoxy-6-(10-(methoxymethoxy)decyl)pyrimidin-5-ol in 5 mL of methanol were added 2 drops of concentrated HCl. The reaction mixture was stirred at reflux for 16 h. The reaction mixture was concentrated under diminished pressure and the residue was purified by chromatography on a silica gel column (8×1 cm). Elution with 1:2 hexanes-ethyl acetate afforded the expected product as white solid: yield 7 mg (40%); mp: 104-105° C.; silica gel TLC Rf 0.15 (1:2 hexanes-ethyl acetate); 1H NMR (methanol-d4) δ 1.28-1.32 (br m, 10H), 1.49 (m, 2H), 1.64 (m, 2H), 2.76 (dd, 2H, J=7.6, 7.6 Hz), 3.22 (s, 6H), 3.51 (t, 2H, J=6.8 Hz) and 4.07 (s, 3H); 13C NMR (methanol-d4) δ 25.55, 27.49, 27.72, 29.02, 29.03, 29.17, 29.19, 29.31, 32.26, 37.20, 37.20, 54.45, 61.59, 128.10, 146.40, 151.34 and 162.67; mass spectrum (APCI+), m/z 326.2442 (M+H) (C17H32N3O3 requires 326.2444).

Workup

  1. temperatureat reflux for 16 h
  2. concentrationThe reaction mixture was concentrated under diminished pressure
  3. customthe residue was purified by chromatography on a silica gel column (8×1 cm)
  4. washElution with 1:2 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-23e88536b78546879baa2a434bad6243
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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