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

HRID 711495

反応式

HRID 711495 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-af85f13051654d38bb8802ef8d546630
出典データセット
uspto-grants-2015_11
特許番号
US09181255B2

関連ノート

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