Water → HCID 14371872, compound

HRID 1381953Notes

Reaction equation

HRID 1381953 reaction equation
O.O1CCOCC1.Cl.[OH:9][N:10]1[C:14](=[O:15])[CH2:13][C:12]2([CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[C:11]1=[O:21].[C:22]([O:26][C:27](SC1N=C(C)C=C(C)N=1)=[O:28])([CH3:25])([CH3:24])[CH3:23]>C(OCC)C.CCCCCC.C(N(CC)CC)C>[C:22]([O:26][C:27]([N:18]1[CH2:17][CH2:16][C:12]2([C:11](=[O:21])[N:10]([OH:9])[C:14](=[O:15])[CH2:13]2)[CH2:20][CH2:19]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 962WaterHCID 312751,4-DioxaneHCID 148428O-(1,1-Dimethylethyl) S-(4,6-dimethyl-2-pyrimidinyl) carbonothioateHCID 21275442HCID 21275442, compound

Product 1

HCID 14371872HCID 14371872, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 21584099Diethylether hexaneSolvent

Procedure

In a mixture solvent consisting of water (50 ml) and dioxane (50 ml) was dissolved 2-hydroxy-2,8-diazaspiro[4,5]decane-1,3-dione.hydrochloride (8.35 g). To the solution were added triethylamine (14 ml) and 2-(tert. butyloxycarbonylthio)-4,6-dimethylpyrimidine (9.6 g). The mixture was stirred for 2 hours at room temperature. The solvent was evaporated off under reduced pressure, and the residual oil was evaporated in 100 ml of ethyl acetate. To the solution was added 100 ml of a saturated aqueous solution of sodium hydrogencarbonate. The aqueous layer was made acid with a solid citric acid, followed by extraction with 100 ml of ethyl acetate. The organic layer was washed with 50 ml of 1N hydrochloric acid and water, which was then dried over anhydrous magnesium sulfate, followed by evaporating off the solvent to leave an oil. This oil was solidified with diethyl ether-n-hexane, which was collected by filtration to obtain 9.6 g of a colorless solid, m.p. 151° to 154° C.

Workup

  1. customThe solvent was evaporated off under reduced pressure
  2. customthe residual oil was evaporated in 100 ml of ethyl acetate
  3. additionTo the solution was added 100 ml of a saturated aqueous solution of sodium hydrogencarbonate
  4. extractionfollowed by extraction with 100 ml of ethyl acetate
  5. washThe organic layer was washed with 50 ml of 1N hydrochloric acid and water, which
  6. dry with materialwas then dried over anhydrous magnesium sulfate
  7. customby evaporating off the solvent
  8. customto leave an oil
  9. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-a848caca15c94432b610008930fb141f
Source dataset
uspto-grants-1989_02
Patent number
US04804665

Reaction notes

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