Triethylamine → Methyl 2-(3-(tert-butoxycarbonylamino)prop-1-ynyl)-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate

HRID 516033

反応式

HRID 516033 の反応式
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]([O:11][CH3:12])=[O:10])=[C:4]([NH:13][C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)[N:3]=1.[CH2:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:22]#[CH:23].C(N(CC)CC)C>CC(N(C)C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[C:27]([O:26][C:25]([NH:24][CH2:21][C:22]#[C:23][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]([O:11][CH3:12])=[O:10])=[C:4]([NH:13][C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)[N:3]=1)=[O:31])([CH3:30])([CH3:29])[CH3:28]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 58317549Methyl 2-chloro-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate

生成物 1

HCID 58317513Methyl 2-(3-(tert-butoxycarbonylamino)prop-1-ynyl)-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate収率 34%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
90 °C

実験手順

Methyl 2-chloro-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate (0.4 g, 1.371 mmol), tert-butyl prop-2-ynylcarbamate (0.426 g, 2.74 mmol), tetrakis(triphenylphosphine)palladium (0.032 g, 0.027 mmol), and copper (I) iodide (0.026 g, 0.137 mmol) was dispersed in DMA (5 mL). Triethylamine (0.382 mL, 2.74 mmol) was added and the mixture was degassed with nitrogen for 5 min. The reaction mixture was placed in a sealed tube and heated at 90° C. for 4 h, after which it was filtered through a pad of Celite, which was rinsed with MeOH. The filtrate was purified via reverse phase preparative HPLC and the fractions were concentrated in vacuo to give the title compound as a brown oil (0.190 g, 34%). [M+H] calc'd for C22H26N4O4, 411; found, 411.

後処理

  1. customthe mixture was degassed with nitrogen for 5 min
  2. customThe reaction mixture was placed in a sealed tube
  3. filtrationafter which it was filtered through a pad of Celite, which
  4. washwas rinsed with MeOH
  5. customThe filtrate was purified via reverse phase preparative HPLC
  6. concentrationthe fractions were concentrated in vacuo

出典と根拠

ORDレコード
ord-0838f3bb52934cddbd7e71d6c612d2b5
出典データセット
uspto-grants-2015_08
特許番号
US09108970B2

関連ノート

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