Triethylamine → (R)-5-iodo-6-methyl-N4-(tetrahydrofuran-3-yl)pyrimidine-2,4-diamine

HRID 421999ノート

反応式

HRID 421999 の反応式
Cl[C:2]1[C:7]([I:8])=[C:6]([CH3:9])[N:5]=[C:4]([NH2:10])[N:3]=1.Cl.[O:12]1[CH2:16][CH2:15][C@@H:14]([NH2:17])[CH2:13]1.C(N(CC)CC)C>CCO.O>[I:8][C:7]1[C:2]([NH:17][C@@H:14]2[CH2:15][CH2:16][O:12][CH2:13]2)=[N:3][C:4]([NH2:10])=[N:5][C:6]=1[CH3:9]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 116447204-Chloro-5-iodo-6-methylpyrimidin-2-amineHCID 46856371(3R)-3-Aminotetrahydrofuran hydrochloride

生成物 1

HCID 59272736(R)-5-iodo-6-methyl-N4-(tetrahydrofuran-3-yl)pyrimidine-2,4-diamine収率 54.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A mixture of 4-chloro-5-iodo-6-methylpyrimidin-2-amine (7.03 g, 26.08 mmol), (R)-tetrahydrofuran-3-amine hydrochloride (Milestone PharmTech, 3.90 g, 31.3 mmol) and triethylamine (9.236 g, 91.3 mmol) in EtOH (150 mL) and water (50 mL) was refluxed for 2-3 days. The reaction was monitored by LC/MS. After completion, the reaction mixture was cooled to ambient temperature and partitioned between 150 mL of ethyl acetate and 200 mL of water. The aqueous layer was extracted by ethyl acetate 3 times. The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. Recrystallization of the residue from ethyl acetate afforded (R)-5-iodo-6-methyl-N4-(tetrahydrofuran-3-yl)pyrimidine-2,4-diamine (4.53 g, 54% yield). MS (EI) for C9H13IN4O: 321.0 (MH+).

後処理

  1. temperaturewas refluxed for 2-3 days
  2. custompartitioned between 150 mL of ethyl acetate and 200 mL of water
  3. extractionThe aqueous layer was extracted by ethyl acetate 3 times
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customRecrystallization of the residue from ethyl acetate

出典と根拠

ORDレコード
ord-51c629c0ed884ffa986947f9f35853ef
出典データセット
uspto-grants-2012_01
特許番号
US08101622B2

反応ノート

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