Triacetoxyperiodinane → N-(4-fluoro-3-methoxybenzyl)-6-formyl-2-methylpyrimidine-4-carboxamide

HRID 572640Notes

Reaction equation

HRID 572640 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:15]=[C:14]([CH2:16][OH:17])[N:13]=[C:12]([CH3:18])[N:11]=2)=[O:9])=[CH:4][C:3]=1[O:21][CH3:22].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:15]=[C:14]([CH:16]=[O:17])[N:13]=[C:12]([CH3:18])[N:11]=2)=[O:9])=[CH:4][C:3]=1[O:21][CH3:22]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 70978675N-(4-fluoro-3-methoxybenzyl)-6-(hydroxymethyl)-2-methylpyrimidine-4-carboxamide

Product 1

HCID 86675901N-(4-fluoro-3-methoxybenzyl)-6-formyl-2-methylpyrimidine-4-carboxamideYield 93.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold solution of N-(4-fluoro-3-methoxybenzyl)-6-(hydroxymethyl)-2-methylpyrimidine-4-carboxamide (7.23 g, 23.71 mmol, Preparation #7) in DCM (150 mL) was added Dess-Martin periodinane (16.10 g, 37.93 mmol, Spectrochem) portion wise over about 45 min at about 0° C. The resulting suspension was allowed to warm to RT and stirred for about another 2 h. The reaction mixture was re-cooled to about 0° C. and quenched with sodiumthiosulphate solution (150 mL) and stirred vigorously for about 30 min. The organic layer was separated, washed successively with saturated sodiumbicarbonate (1×100 mL), water (1×150 mL) and brine (1×150 mL), dried over sodium sulphate and concentrated under reduced pressure to afford N-(4-fluoro-3-methoxybenzyl)-6-formyl-2-methylpyrimidine-4-carboxamide 6.75 g (crude 94%), 1H NMR (400 MHz, DMSO): δ 9.99 (s, 1H), 9.586-9.556 (t, J=6.4 Hz, 1H), 8.09 (s, 1H), 7.18-7.11 (m, 2H), 6.90-6.87 (m, 1H), 4.495-4.479 (d, J=6.4 Hz, 2H), 3.81 (s, 3H), 2.84 (s, 3H), MS m/z: 304.2 (M+H)+.

Workup

  1. temperatureThe reaction mixture was re-cooled to about 0° C.
  2. customquenched with sodiumthiosulphate solution (150 mL)
  3. stirringstirred vigorously for about 30 min
  4. customThe organic layer was separated
  5. washwashed successively with saturated sodiumbicarbonate (1×100 mL), water (1×150 mL) and brine (1×150 mL)
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7521f2d38777476fb7aacbb979fd3bbd
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

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