Guanidine Hydrochloride → Methyl 2-amino-6,7-dihydro-5H-cyclopenta[d]pyrimidine-6-carboxylate

HRID 2175902노트

반응식

HRID 2175902 반응식
CN([CH:4]=[C:5]1[C:9](=O)[CH2:8][CH:7]([C:11]([O:13][CH3:14])=[O:12])[CH2:6]1)C.Cl.[NH2:16][C:17]([NH2:19])=[NH:18].C[O-].[Na+]>CO>[NH2:18][C:17]1[N:19]=[CH:4][C:5]2[CH2:6][CH:7]([C:11]([O:13][CH3:14])=[O:12])[CH2:8][C:9]=2[N:16]=1

참가 물질

5

반응물 3

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 86727100Methyl 3-[(dimethylamino)methylidene]-4-oxocyclopentanecarboxylate

생성물 1

HCID 86727099Methyl 2-amino-6,7-dihydro-5H-cyclopenta[d]pyrimidine-6-carboxylate

시약·촉매·용매 1

HCID 887Methanol용매2회

반응 조건

온도
90 °C

실험 절차

To a solution of methyl 3-[(dimethylamino)methylidene]-4-oxocyclopentanecarboxylate (71.7 mg, 0.36 mmol) in anhydrous methanol (2.5 mL) was added guanidine hydrochloride (124.7 mg, 1.3 mmol) followed by sodium methoxide in methanol (0.24 mL, 1.27 mmol). The mixture was heated to 90° C. in a sealed tube overnight. The crude reaction was quenched with 2 N HCl and concentrated in vacuo. The aqueous residue was purified by HPLC (30×100 mm Waters Sunfire column; 5 micron; 35 mL/min.; 210 nM; 0% to 40% CH3CN+0.05% TFA/water+0.05% TFA over 15 min.; the compound eluted at 10% CH3CN+0.05% TFA/water+0.05% TFA) to afford the title compound after lyophilization.

후처리

  1. customThe crude reaction
  2. customwas quenched with 2 N HCl
  3. concentrationconcentrated in vacuo
  4. customThe aqueous residue was purified by HPLC (30×100 mm Waters Sunfire column
  5. washthe compound eluted at 10% CH3CN+0.05% TFA/water+0.05% TFA)

출처 및 근거

ORD 기록
ord-dee21f97baec43fe97cf9bd7ab342a77
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062070B2

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