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

HRID 2175902ノート

反応式

HRID 2175902 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
90 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-dee21f97baec43fe97cf9bd7ab342a77
出典データセット
uspto-grants-2015_06
特許番号
US09062070B2

反応ノート

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