Triethylamine → 5-Chloro-1-{[(1,2,5-thiadiazol-3-yl)methoxy]methyl}pyrimidin-2(1H)-one

HRID 1719243Notes

Reaction equation

HRID 1719243 reaction equation
Cl[CH2:2][O:3][CH2:4][C:5]1[CH:9]=[N:8][S:7][N:6]=1.Cl.[Cl:11][C:12]1[CH:13]=[N:14][C:15](=[O:18])[NH:16][CH:17]=1.C(N(CC)CC)C>ClCCl>[S:7]1[N:8]=[CH:9][C:5]([CH2:4][O:3][CH2:2][N:16]2[CH:17]=[C:12]([Cl:11])[CH:13]=[N:14][C:15]2=[O:18])=[N:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 126485235-Chloropyrimidin-2-ol hydrochlorideHCID 202679333-[(Chloromethoxy)methyl]-1,2,5-thiadiazole

Product 1

HCID 202679415-Chloro-1-{[(1,2,5-thiadiazol-3-yl)methoxy]methyl}pyrimidin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

3-(Chloromethyl)oxymethyl-1,2,5-thiadiazole (see Preparation 10) (0.18 mmol) in dichloromethane (1 ml) was added dropwise with stirring at room temperature to a solution of 5-chloropyrimidin-2-one hydrochloride (18 mmol) and triethylamine (0.36 mmol) in dichloromethane (3 ml). The mixture was stirred for 11/2 hours at 40° C. before the solvent was distilled off. The residue was triturated with water, extracted into chloroform and the dried (MgSO4) solution evaporated. Trituration of the residue with ether left the title compound in 20% (11 mg) yield, m.p. 106° C. 1H NMR (CDCl3): δ5.00 (CH2Het), 5.40 (OCH2), 7.73 and 8.47 (H-4, H-6, J 3 Hz), 8.50 (H-31).

Workup

  1. distillationwas distilled off
  2. customThe residue was triturated with water
  3. extractionextracted into chloroform
  4. dry with materialthe dried (MgSO4) solution
  5. customevaporated
  6. waitTrituration of the residue with ether left the title compound in 20% (11 mg)
  7. customyield

Sources & evidence

ORD record
ord-756a1ffcc1ea4771b3b408be02f6035e
Source dataset
uspto-grants-1985_09
Patent number
US04539324

Reaction notes

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