Cyclopentylamine → N4-cyclopentylpyrimidine-2,4-diamine

HRID 79191

반응식

HRID 79191 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 58299890N4-cyclopentylpyrimidine-2,4-diamine수율 84.5%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
105 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-50f69fdebf1f4b2284aa376c6e2cf73c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841312B2

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