Phosphorus oxychloride → HCID 77134375, compound

HRID 1696575Notes

Reaction equation

HRID 1696575 reaction equation
O=P(Cl)(Cl)[Cl:3].[C:6]([C:10]1[N:15]=[C:14](O)[C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][N:11]=1)([CH3:9])([CH3:8])[CH3:7]>CCN(CC)CC>[C:6]([C:10]1[N:15]=[C:14]([Cl:3])[C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][N:11]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178498799HCID 178498799, compound

Product 1

HCID 77134375HCID 77134375, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
40 °C

Procedure

To ice cold (0-5° C.) POCl3 (35 mL) was added dropwise Et3N (0.4 mL), followed by methyl 2-t-butyl-4-hydroxypyrimidine-5-carboxylate (3.45 g, 16.4 mmol). The mixture was then warmed to 40° C. and stirred under Ar for 1 h, then concentrated and diluted with CHCl3 (100 mL) and poured carefully onto ice (˜300 g) and stirred at RT until the ice all melted. The organic phase was separated, washed with NaHCO3 (100 mL), H2O (100 mL), dried (Na2SO4), concentrated and dried to yield methyl 2-t-butyl-4-chloropyrimidine-5-carboxylate (3.28 g, 87% yield). 1H NMR (400 MHz, DMSO-d6): δ 1.35 (s, 9H), 3.90 (s, 3H), 9.14 (s, 1H).

Workup

  1. concentrationconcentrated
  2. additiondiluted with CHCl3 (100 mL)
  3. additionpoured carefully onto ice (˜300 g)
  4. stirringstirred at RT until the ice
  5. customThe organic phase was separated
  6. washwashed with NaHCO3 (100 mL), H2O (100 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customdried

Sources & evidence

ORD record
ord-edd2528378174313a8c13a4c0336c6a4
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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