Ethyl 4-chloro-2-methylpyrimidine-5-carboxylate → Ethyl 2-methyl-4-{N-butyl-N-[{2'-(N-triphenylmethyltetrazol-5-yl)biphenyl-4-yl}methyl]amino}pyrimidine-5-carboxylate

HRID 1030061노트

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HRID 1030061 반응식
[C:1]1([C:7]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]3[CH:24]=[CH:23][C:22]([CH2:25][NH:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:21][CH:20]=3)=[N:11][N:10]=[N:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:43]([O:45][C:46]([C:48]1[C:49](Cl)=[N:50][C:51]([CH3:54])=[N:52][CH:53]=1)=[O:47])[CH3:44]>C1COCC1.C(N(CC)CC)C>[CH3:54][C:51]1[N:50]=[C:49]([N:26]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:25][C:22]2[CH:23]=[CH:24][C:19]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12]3[N:8]([C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:9]=[N:10][N:11]=3)=[CH:20][CH:21]=2)[C:48]([C:46]([O:45][CH2:43][CH3:44])=[O:47])=[CH:53][N:52]=1

참가 물질

5

반응물 2

HCID 12677176Ethyl 4-chloro-2-methylpyrimidine-5-carboxylateHCID 19821739N-Triphenylmethyl-5-(4'-butylaminomethylbiphenyl-2-yl)tetrazole

생성물 1

HCID 19791910Ethyl 2-methyl-4-{N-butyl-N-[{2'-(N-triphenylmethyltetrazol-5-yl)biphenyl-4-yl}methyl]amino}pyrimidine-5-carboxylate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8471Triethylamine용매

실험 절차

The product of Example 1A was dissolved in 15 ml of THF containing 4.6 ml of triethylamine. A solution of 1.94 g (9.7 mmoles) of ethyl-2-methyl-4-chloropyrimidine-5-carboxylate (E. Peters, et al., J. Org. Chem. 25 2137 (1960)) in 2 ml of THF was added and the resulting solution was stirred at room temperature for 2 hours. The solution was then concentrated and the resulting residue was dissolved in toluene. The toluene solution was extracted with potassium bicarbonate, dried over sodium sulfate and concentrated. The crude product was chromatographed on silica gel eluting with 12% ethyl acetate/88%toluene to provide 4.97 g of the desired product, which was crystallized from ether/hexane (1:1). M.p. 130°-132° C.

후처리

  1. concentrationThe solution was then concentrated
  2. dissolutionthe resulting residue was dissolved in toluene
  3. extractionThe toluene solution was extracted with potassium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was chromatographed on silica gel eluting with 12% ethyl acetate/88%toluene

출처 및 근거

ORD 기록
ord-5498374cdf08456bb3e5493066efbb95
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05104877

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