Formaldehyde → HCID 67328968, compound

HRID 1846191Notes

Reaction equation

HRID 1846191 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[N:11][C:12](N)=[N:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:33]=O.[BH3-][C:36]#[N:37].[Na+]>CO>[CH2:1]([O:8][C:9]1[C:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[N:11][C:12]([N:37]([CH3:36])[CH3:33])=[N:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67329050HCID 67329050, compound

Product 1

HCID 67328968HCID 67328968, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred solution containing 230 mg (0.52 mmol) of 5-(benzyloxy)-4-hexadecyl-6-methylpyrimidin-2-amine in 4 mL of methanol were added 4 mL of 35% aq. formaldehyde followed by 263 mg (4.18 mmol) of NaCNBH3. The reaction mixture was stirred at 23° C. for 3 h. The reaction mixture was quenched with acetic acid until bubbling ceased then poured into 20 mL of water and extracted with two 40-mL portions of ethyl acetate. The combined organic layer was washed with one 40-mL portion of saturated aq. NaHCO3 and one 40-mL portion of brine. The organic solution was dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (8×3 cm). Elution with 4:1 hexanes-ethyl acetate afforded the expected product as colorless oil: yield 100 mg (41%); silica gel TLC Rf 0.75 (4:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 0.86 (t, 3H, J=6.8 Hz), 1.23-1.28 (br m, 26H), 1.68 (quint, 2H, J=6.8 Hz), 2.31 (s, 3H), 2.61 (dd, 2H, J=7.6, 7.6 Hz), 3.14 (s, 6H), 4.69 (s, 2H) and 7.40-7.46 (m, 5H); 13C NMR (CDCl3) δ 14.05, 19.29, 22.64, 27.72, 27.84, 29.31, 29.50, 29.55, 29.62, 29.64, 29.64, 29.64, 29.66, 29.66, 29.66, 31.59, 31.70, 31.89, 37.21, 37.21, 75.67, 127.90, 128.16, 128.16, 128.54, 128.54, 137.17, 141.27, 158.60, 159.01 and 163.62; mass spectrum (APCI), m/z 468.3950 (M+H)+ (C30H50N3O requires 468.3954).

Workup

  1. customThe reaction mixture was quenched with acetic acid
  2. customuntil bubbling
  3. additionceased then poured into 20 mL of water
  4. extractionextracted with two 40-mL portions of ethyl acetate
  5. washThe combined organic layer was washed with one 40-mL portion of saturated aq. NaHCO3 and one 40-mL portion of brine
  6. dry with materialThe organic solution was dried (MgSO4)
  7. concentrationconcentrated under diminished pressure
  8. customThe residue was purified by chromatography on a silica gel column (8×3 cm)
  9. washElution with 4:1 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-bcdb5e7ba5984ce6a263990c168245ae
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

Loading…