Methyl iodide → 1-methyl-2-methylsulfanyl-5-pyrimidin-5-ylmethyl-1H-pyrimidin-4-one

HRID 474721노트

반응식

HRID 474721 반응식
[CH3:1][S:2][C:3]1[NH:4][CH:5]=[C:6]([CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[N:15][CH:16]=2)[C:7](=[O:9])[N:8]=1.[CH3:17]I>C1COCC1.[H-].[Na+]>[CH3:17][N:4]1[CH:5]=[C:6]([CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[N:15][CH:16]=2)[C:7](=[O:9])[N:8]=[C:3]1[S:2][CH3:1]

참가 물질

5

반응물 2

HCID 6328Methyl iodideHCID 178503543HCID 178503543, 화합물

생성물 1

HCID 677748841-methyl-2-methylsulfanyl-5-pyrimidin-5-ylmethyl-1H-pyrimidin-4-one수율 48.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 24758Sodium hydride용매

실험 절차

2-Methylsulfanyl-5-pyrimidin-5-ylmethyl-1H-pyrimidin-4-one (50 mg, 0.213 mmol, 1 eq) was dissolved in dry THF (0.7 ml) and NaH, 60% (24.7 mg, 0.618 mmol, 2.9 eq) was added. After 30 min, the reaction mixture was treated with methyl iodide (133 μl, 2.13 mmol, 10 eq) and was stirred overnight. After overnight the excess NaH was quenched by a slow addition of water, diluted with brine (30 ml) and extracted with Et2O (3×20 ml). Combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated to give a crude residue. Crude residue was purified via Biotage SP-1 Snap Si 10 g; 15 ml/min in the gradient of MeoH in DCM: 1% for 1 CV then from 1-5% for 20 CV. The appropriate fractions were combined and evaporated in vacuo to give the required product 1-methyl-2-methylsulfanyl-5-pyrimidin-5-ylmethyl-1H-pyrimidin-4-one (25.5 mg, yield=47.4%, purity=98%). [M+H]+=249.31 1H NMR (300 MHz; DMSO-d6) δ/ppm 2.49 (s, 3H), 3.53 (s, 3H), 3.58 (s, 2H), 7.80 (s, 1H), 8.72 (s, 2H), 9.03 (s, 1H)

후처리

  1. customAfter overnight the excess NaH was quenched by a slow addition of water
  2. additiondiluted with brine (30 ml)
  3. extractionextracted with Et2O (3×20 ml)
  4. dry with materialCombined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a crude residue
  8. customCrude residue was purified via Biotage SP-1 Snap Si 10 g
  9. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-eb34a5055b6643aaa3a11e0b9b6e6219
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637536B2

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