Hydrochloric Acid → HCID 53373130, compound

HRID 1846180Notes

Reaction equation

HRID 1846180 reaction equation
C([O:8][C:9]1[C:10]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28]COC)=[N:11][C:12]([O:16][CH3:17])=[N:13][C:14]=1[CH3:15])C1C=CC=CC=1.Cl>CO.[OH-].[OH-].[Pd+2]>[OH:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:10]1[C:9]([OH:8])=[C:14]([CH3:15])[N:13]=[C:12]([O:16][CH3:17])[N:11]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67329649HCID 67329649, compound

Product 1

HCID 53373130HCID 53373130, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution containing 30.0 mg (0.07 mmol) of 5-(Benzyloxy)-2-methoxy-4-(10-(methoxymethoxy)decyl)-6-methylpyrimidine in 3 mL of methanol was added a drop of concentrated HCl. The mixture was stirred at reflux for 16 h. Then, were added 2 mg of 20% palladium hydroxide on carbon (Degussa type E101 NE/N) and the mixture was stirred at 23° C. for 20 min. The mixture was filtered through celite and concentrated under diminished pressure to afford the expected product as a yellowish oil: yield 20 mg (97%); silica gel TLC Rf 0.45 (4:1 hexanes-ethyl acetate); 1H NMR (methanol) δ 1.30 (br m, 12H), 1.50 (br m, 2H), 1.74 (br m, 2H), 2.56 (s, 3H), 2.89 (dd, 2H, J=7.6, 7.6 Hz), 3.51 (t, 2H, J=6.4 Hz) and 4.15 (s, 3H); 13C NMR (methanol) δ 16.16, 25.49, 26.83, 28.94, 29.04, 29.11, 29.18, 29.22, 30.82, 32.20, 56.14, 61.56, 143.11, 143.11, 152.95 and 152.95; mass spectrum (APCI), m/z (M+H)+ 297.2180 (C16H29N2O3 requires 297.2178).

Workup

  1. temperatureat reflux for 16 h
  2. stirringthe mixture was stirred at 23° C. for 20 min
  3. filtrationThe mixture was filtered through celite
  4. concentrationconcentrated under diminished pressure

Sources & evidence

ORD record
ord-5082de4386b142ac9e9a6a3be857ae00
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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