Diisopropylethylamine → HCID 178446422、化合物

HRID 2169336ノート

反応式

HRID 2169336 の反応式
[CH2:1]([O:8][C:9]1[C:10]([C:28](O)=[O:29])=[N:11][C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:31]([O:38][CH2:39][CH2:40][NH:41][CH2:42][C:43]([CH3:46])([CH3:45])[CH3:44])([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.O>[Si:31]([O:38][CH2:39][CH2:40][N:41]([CH2:42][C:43]([CH3:46])([CH3:45])[CH3:44])[C:28]([C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:14]([OH:15])[N:13]=[C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:11]=1)=[O:29])([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:32])[CH3:33]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86725974[2-(tert-Butyl-dimethylsilanyloxy)-ethyl]-(2,2-dimethyl-propyl)-amineHCID 178524866HCID 178524866、化合物

生成物 1

HCID 178446422HCID 178446422、化合物収率 86.27%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution mixture of 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (283) (230 mg, 0.57 mmol) and [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-(2,2-dimethyl-propyl)-amine (8h) (167 mg, 0.68 mmol) in dimethylformamide (2.2 mL) were added N,N-diisopropylethylamine (0.3 mL, 1.70 mmol) and HATU (324 mg, 0.85 mmol). The reaction was stirred at room temperature for 20 h. Water (75 mL) was added and the mixture was extracted with ethyl acetate (3×20 mL). The combined organic part was washed with water (3×50 mL) and brine (2×30 mL) and dried and concentrated. The crude product was purified by Combi-Flash column (eluted at 20-30% ethyl acetate in hexane) to get 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-(2,2-dimethyl-propyl)-amide (300) (310 mg, 86.27%) as an off-white sticky solid.

後処理

  1. extractionthe mixture was extracted with ethyl acetate (3×20 mL)
  2. washThe combined organic part was washed with water (3×50 mL) and brine (2×30 mL)
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was purified by Combi-Flash column (eluted at 20-30% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-83f6b7fcd84f4a578d61347192dae877
出典データセット
uspto-grants-2015_06
特許番号
US09045486B2

反応ノート

読み込み中…