Hydrochloric Acid → 3-[5-(2,4-dimethyl-1,3-thiazol-5-yl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]propanal

HRID 1925037Notes

Reaction equation

HRID 1925037 reaction equation
C[O:2][CH:3](OC)[CH2:4][CH2:5][N:6]1[CH:11]=[C:10]([C:12]2[S:16][C:15]([CH3:17])=[N:14][C:13]=2[CH3:18])[C:9](=[O:19])[NH:8][C:7]1=[O:20].Cl.C(N(CC)CC)C>O1CCCC1>[CH3:17][C:15]1[S:16][C:12]([C:10]2[C:9](=[O:19])[NH:8][C:7](=[O:20])[N:6]([CH2:5][CH2:4][CH:3]=[O:2])[CH:11]=2)=[C:13]([CH3:18])[N:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 594483571-[3,3-bis(methyloxy)propyl]-5-(2,4-dimethyl-1,3-thiazol-5-yl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 594483663-[5-(2,4-dimethyl-1,3-thiazol-5-yl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]propanal

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
45 °C

Procedure

1-[3,3-bis(methyloxy)propyl]-5-(2,4-dimethyl-1,3-thiazol-5-yl)-2,4(1H,3H)-pyrimidinedione (Prep35, 321 mg, 0.987 mmol) was dissolved in Tetrahydrofuran (THF) (20 mL), 1N Hydrochloric acid aqueous solution (5.92 mL, 5.92 mmol) was added and the mixture was stirred at 45° C. for 1.5 hours. Volatiles were evaporated under vacuum (cold bath) then triethylamine (0.825 mL, 5.92 mmol) and THF (6 mL) were added. Solvents were eliminated until dryness and the white foam thus obtained was used in the next step without further purification.

Workup

  1. customVolatiles were evaporated under vacuum (cold bath)
  2. customthe white foam thus obtained
  3. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-fab5116226dd4667b92c060eb4256009
Source dataset
uspto-grants-2012_05
Patent number
US08178549B2

Reaction notes

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