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 1030061ノート

反応式

HRID 1030061 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5498374cdf08456bb3e5493066efbb95
出典データセット
uspto-grants-1992_04
特許番号
US05104877

反応ノート

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