Formaldehyde → HCID 67328276, compound

HRID 1846187Notes

Reaction equation

HRID 1846187 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][CH3:26])=[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.[CH2:27]=O.[BH3-][C:30]#[N:31].[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][CH3:26])=[N:11][C:12]([N:31]([CH3:30])[CH3:27])=[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 67328339HCID 67328339, compound

Product 1

HCID 67328276HCID 67328276, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred solution containing 305 mg (0.86 mmol) of 5-(benzyloxy)-4-decyl-6-methylpyrimidin-2-amine in 3 mL of methanol were added 3 mL of 35% aq. formaldehyde followed by 271 mg (4.30 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 2:1 hexanes-ethyl acetate afforded the expected product as colorless oil: yield 154 mg (46%); silica gel TLC Rf 0.8 (2:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 0.87 (t, 3H, J=6.4 Hz), 1.33 (m, 14H), 1.69 (quint, 2H, J=7.2 Hz), 2.32 (s, 3H), 2.61 (dd, 2H, J=7.6, 7.6 Hz), 3.14 (s, 6H), 4.70 (s, 2H) and 7.33-7.44 (m, 5H); 13C NMR (CDCl3) δ 14.07, 19.29, 22.65, 27.85, 29.30, 29.50, 29.55, 29.59, 29.62, 31.71, 31.89, 37.21, 37.21, 75.72, 127.91, 128.11, 128.11, 128.54, 128.54, 137.17, 141.27, 158.60, 159.01 and 163.49; mass spectrum (APCI), m/z 384.3003 (M+H)+ (C24H38N3O requires 384.3015).

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 2:1 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-9838b7baf8094cdaa8707b6b2dd8a2ec
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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