Cyclopentylamine → N4-cyclopentylpyrimidine-2,4-diamine

HRID 79191

反応式

HRID 79191 の反応式
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH:9]1([NH2:14])[CH2:13][CH2:12][CH2:11][CH2:10]1.C(N(CC)CC)C>CCO>[CH:9]1([NH:14][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

参加物

5

反応物 3

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 2233322-Amino-4-chloropyrimidine

生成物 1

HCID 58299890N4-cyclopentylpyrimidine-2,4-diamine収率 84.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
105 °C

実験手順

A mixture of 2-amino-4-chloropyrimidine (22.8 g, 176 mmol), cyclopentylamine (20.9 mL, 211 mmol) and triethylamine (29.4 mL, 211 mmol) in EtOH (200 mL) was heated at reflux (105° C., oil bath) for 48 h. Upon workup, the volatile was removed in vacuo. The residue was poured into ice and saturated Na2CO3 aqueous solution and extracted with ethyl acetate (3×). The combined organics were washed with saturated Na2CO3 aqueous solution (1×), dried over Na2SO4, and concentrated in vacuo to give N4-cyclopentylpyrimidine-2,4-diamine (315) (26.5 g) as a light yellow solid of 92% purity. This batch of material was taken onto the next step without further purification. LCMS-ESI (POS), M/Z, M+1: Found 179.1, Calculated 179.1.

後処理

  1. temperaturewas heated
  2. customUpon workup, the volatile was removed in vacuo
  3. additionThe residue was poured into ice and saturated Na2CO3 aqueous solution
  4. extractionextracted with ethyl acetate (3×)
  5. washThe combined organics were washed with saturated Na2CO3 aqueous solution (1×)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-50f69fdebf1f4b2284aa376c6e2cf73c
出典データセット
uspto-grants-2014_09
特許番号
US08841312B2

関連ノート

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