Hydrogen Peroxide → 2-(bicyclo[1.1.1]pentan-1-ylamino)-4-((1R,3R,4R)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide

HRID 2280754ノート

反応式

HRID 2280754 の反応式
[C:1]12([NH:6][C:7]3[N:12]=[C:11]([NH:13][C@@H:14]4[CH2:19][CH2:18][C@@H:17]([CH3:20])[C@H:16]([OH:21])[CH2:15]4)[C:10]([C:22]#[N:23])=[CH:9][N:8]=3)[CH2:5][CH:3]([CH2:4]1)[CH2:2]2.[OH-:24].[Na+].OO>CS(C)=O>[C:1]12([NH:6][C:7]3[N:12]=[C:11]([NH:13][C@@H:14]4[CH2:19][CH2:18][C@@H:17]([CH3:20])[C@H:16]([OH:21])[CH2:15]4)[C:10]([C:22]([NH2:23])=[O:24])=[CH:9][N:8]=3)[CH2:2][CH:3]([CH2:4]1)[CH2:5]2

参加物

5

反応物 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 712373672-(bicyclo[1.1.1]pentan-1-ylamino)-4-((1R,3R,4R)-3-hydroxy-4-methylcyclohexylamino)pyrimidine-5-carbonitrile

生成物 1

HCID 712370942-(bicyclo[1.1.1]pentan-1-ylamino)-4-((1R,3R,4R)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide収率 67%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
50 °C

実験手順

2-(Bicyclo[1.1.1]pentan-1-ylamino)-4-((1R,3R,4R)-3-hydroxy-4-methylcyclohexylamino)pyrimidine-5-carbonitrile (0.38 g, 1.213 mmol) was dissolved in DMSO (26.9 mL) and to this solution was added a 50% aqueous sodium hydroxide solution (0.097 ml, 1.213 mmol) and a 30% aqueous hydrogen peroxide solution 0.137 mL, 1.213 mmol) at room temperature. Then the reaction mixture was stirred at 50° C. for 1 h. The reaction was cooled to room temperature and it was poured into 50 mL of ice water. The white precipitate was collected on filter paper and was washed twice with water. The precipitate was dried to give 2-(bicyclo[1.1.1]pentan-1-ylamino)-4-((1R,3R,4R)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide (0.269 g, 0.812 mmol, 67% yield). 1H NMR (DMSO-d6, 400 MHz): δ ppm 0.94 (d, J=6.25 Hz, 3H) 1.10-1.26 (m, 3H) 1.68 (d, J=10.54 Hz, 1H) 1.92 (d, J=10.93 Hz, 1H) 2.06 (s, 6H) 2.17 (d, J=9.76 Hz, 1H) 2.46 (s, 1H) 2.98 (br. s., 1H) 3.82-3.95 (m, 1H) 4.63 (br. s., 1H) 7.16 (br. s., 1H) 7.77 (br. s., 1H) 8.11 (br. s., 1H) 8.33 (s, 1H) 9.24 (br. s., 1H); MS (ESI): m/z 332.3 [M+1]+.

後処理

  1. customat room temperature
  2. temperatureThe reaction was cooled to room temperature
  3. customThe white precipitate was collected
  4. filtrationon filter paper
  5. washwas washed twice with water
  6. customThe precipitate was dried

出典と根拠

ORDレコード
ord-fe76691505f24bf8a79758528f14e9dd
出典データセット
uspto-grants-2015_09
特許番号
US09139534B2

反応ノート

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