Lithium Hydroxide → 6-(Cyclopentylamino)pyrimidine-4-carboxylic acid

HRID 1746646ノート

反応式

HRID 1746646 の反応式
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[C:4]([NH:12][CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16]C2)[N:3]=1.C(N(CC)CC)C.C1(NC2N=CN=C(C(OC)=O)C=2)CCCC1.C1(NC2N=CN=C(C(OCC)=O)C=2)CCCC1.[OH-].[Li+]>[Pd].CCO.C1COCC1.CCO.O.O>[CH:13]1([NH:12][C:4]2[N:3]=[CH:2][N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=2)[CH2:14][CH2:18][CH2:17][CH2:16]1

参加物

10

反応物 5

HCID 3939Lithium HydroxideHCID 8471TriethylamineHCID 67528393Methyl 6-(cyclopentylamino)pyrimidine-4-carboxylateHCID 67529171Ethyl 6-(cyclopentylamino)pyrimidine-4-carboxylateHCID 86644304HCID 86644304、化合物2 回

生成物 1

HCID 594470556-(Cyclopentylamino)pyrimidine-4-carboxylic acid

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 18504229Ethanol tetrahydrofuran water溶媒

実験手順

A mixture of methyl 2-chloro-6-[(cyclopentylmethyl)amino]pyrimidine-4-carboxylate (Intermediate 2, 2.00 g; 7.82 mmol; 1.00 eq.), palladium on charcoal (750 mg) and triethylamine (3.27 mL; 23.5 mmol) in EtOH (200 mL) was stirred under an atmosphere of hydrogen for 2 hours. After 2 hours the reaction mixture was filtered on celite and evaporated to give a mixture of methyl 6-(cyclopentylamino)pyrimidine-4-carboxylate and ethyl 6-(cyclopentylamino)pyrimidine-4-carboxylate. The crude mixture was dissolved in a mixture of THF/EtOH/H2O (3/2/1, 120 mL) and treated with an aqueous solution of lithium hydroxide (1N, 23.5 mL, 23.5 mmol). The reaction mixture was stirred at RT for 60 minutes. Water was added (50 mL) and the aqueous layer was washed with DCM (30 mL). The aqueous layer was acidified to pH 5 by addition of an HCl solution (1N). The aqueous layer was evaporated in vacuo to reduce the volume by 30-50%. The resulting white solid was filtered to afford the title compound as a white solid.

後処理

  1. filtrationAfter 2 hours the reaction mixture was filtered on celite
  2. customevaporated
  3. customto give
  4. stirringThe reaction mixture was stirred at RT for 60 minutes
  5. washthe aqueous layer was washed with DCM (30 mL)
  6. additionThe aqueous layer was acidified to pH 5 by addition of an HCl solution (1N)
  7. customThe aqueous layer was evaporated in vacuo
  8. filtrationThe resulting white solid was filtered

出典と根拠

ORDレコード
ord-ff3085315da44194bcf5dbeb1e6a8c53
出典データセット
uspto-grants-2015_10
特許番号
US09150519B2

反応ノート

読み込み中…