Triethylamine → N-methoxy-N-methyl-2-(methylthio)pyrimidine-4-carboxamide

HRID 1455238

반응식

HRID 1455238 반응식
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]([OH:11])=O)[CH:6]=[CH:5][N:4]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl.[CH3:36][NH:37][O:38][CH3:39].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CC#N>[CH3:39][O:38][N:37]([CH3:36])[C:9]([C:7]1[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=1)=[O:11]

참가 물질

8

반응물 6

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2957752-(Methylsulfanyl)pyrimidine-4-carboxylic acidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 21948429N-methoxy-N-methyl-2-(methylthio)pyrimidine-4-carboxamide수율 89%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a slurry of 2-methylsulfanyl-pyrimidine-4-carboxylic acid (10.0 g, 59.2 mmol) in CH3CN (300 mL) is added in sequence: 1-hydroxybenzotriazole hydrate (9.59 g, 71.0 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (13.6 g, 71.0 mmol), N,O-dimethylhydroxylamine hydrochloride (8.66 g, 88.8 mmol), and triethylamine (Et3N) (24.9 mL, 178 mmol). The resulting slurry is stirred overnight at ambient temperature. After 16 hours, the reaction mixture is poured into a saturated aqueous solution of sodium bicarbonate (300 mL) and the layers separated. The aqueous layer is extracted with ethyl acetate (3×250 mL). The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo and the resulting residue is purified over silica (100% EtOAc) to afford 10.1 g (89% yield) of the desired product as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 8.65 (d, J=4.9 Hz, 1H), 7.15 (br s, 1H), 3.77 (br s, 3H), 3.38 (br s, 3H), 2.61 (s, 3H); MS (ESI) m/z 214 (M+1).

후처리

  1. waitAfter 16 hours
  2. customthe layers separated
  3. extractionThe aqueous layer is extracted with ethyl acetate (3×250 mL)
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe resulting residue is purified over silica (100% EtOAc)

출처 및 근거

ORD 기록
ord-634c3a38036a42ff89a13908cee81827
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482356B2

연결된 노트

불러오는 중…