Sodium hydride → (R)-tetrahydrofuran-3-yl 4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate

HRID 1478287ノート

反応式

HRID 1478287 の反応式
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]4[CH:25]=[CH:24]C([N+]([O-])=O)=C[CH:21]=4)=[O:18])[CH2:13][CH2:12]3)=[N:7][C:6]=12.[O:29]1CC[C@@H](O)C1.[H-].[Na+]>C1COCC1.CCOC(C)=O>[O:29]1[CH2:24][CH2:25][C@@H:20]([O:19][C:17]([N:14]2[CH2:15][CH2:16][N:11]([C:8]3[CH:9]=[CH:10][N:5]4[N:4]=[CH:3][C:2]([Br:1])=[C:6]4[N:7]=3)[CH2:12][CH2:13]2)=[O:18])[CH2:21]1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 641512(-)-3-HydroxytetrahydrofuranHCID 866974514-Nitrophenyl 4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate

生成物 1

HCID 86697452(R)-tetrahydrofuran-3-yl 4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate収率 72%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To 112 mg (0.25 mmol) of 4-nitrophenyl 4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate dissolved in 10 mL of THF, was added (R)-tetrahydrofuran-3-ol (44 mg, 0.5 mmol), followed by 60% NaH (40 mg, 1.0 mmol) and stirred at RT for 2 hr. After 2 hr it was diluted with 20 mL of EtOAc and slowly quench with brine. The organic layer was dried over MgSO4 and concentrated, it was purified over 12 gram silica gel column eluting with 0-10% MeOH/DCM to obtain 71 mg (72% yield) of the desired product.

後処理

  1. customslowly quench with brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customit was purified over 12 gram silica gel column
  5. washeluting with 0-10% MeOH/DCM

出典と根拠

ORDレコード
ord-12d4ddde1ee440eb8ece60091c5ec51a
出典データセット
uspto-grants-2016_08
特許番号
US09403832B2

反応ノート

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