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

HRID 1925041Notes

Reaction equation

HRID 1925041 reaction equation
C[O:2][CH:3](OC)[CH2:4][CH2:5][N:6]1[CH:11]=[C:10]([C:12]2[S:13][CH:14]=[C:15]([CH3:17])[N:16]=2)[C:9](=[O:18])[NH:8][C:7]1=[O:19].Cl>O1CCCC1>[CH3:17][C:15]1[N:16]=[C:12]([C:10]2[C:9](=[O:18])[NH:8][C:7](=[O:19])[N:6]([CH2:5][CH2:4][CH:3]=[O:2])[CH:11]=2)[S:13][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 594483511-[3,3-bis(methyloxy)propyl]-5-(4-methyl-1,3-thiazol-2-yl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 594483593-[5-(4-methyl-1,3-thiazol-2-yl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]propanal

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-[3,3-bis(methyloxy)propyl]-5-(4-methyl-1,3-thiazol-2-yl)-2,4(1H,3H)-pyrimidinedione (Pre 44, 34 mg, 0.109 mmol) in Tetrahydrofuran (THF) (1.5 ml) 1M aqueous HCl (0.546 ml, 0.546 mmol) was added and the mixture was stirred at rt for 5 hrs. Other 1M aqueous HCl (0.273 ml, 0.273 mmol) was added and the mixture was stirred at rt overnight. Volatiles were evaporated (rotary, cold bath) and the residue was taken up with TEA (0.122 ml, 0.874 mmol) and THF (3 mL). The slurry was evaporated to dryness (rotary) to afford a crude that was used in the next reaction step assuming quantitative conversion to target compound (0.109 mmol) without any further purification

Workup

  1. stirringthe mixture was stirred at rt overnight
  2. customVolatiles were evaporated (rotary, cold bath)
  3. customThe slurry was evaporated to dryness (rotary)
  4. customto afford a crude that
  5. customwas used in the next reaction step
  6. customwithout any further purification

Sources & evidence

ORD record
ord-70ed00e04e6b4ef2baa98aec6a2de9c9
Source dataset
uspto-grants-2012_05
Patent number
US08178549B2

Reaction notes

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