Bromomethylcyclopropane → 2-Chloro-5-(cyclopropylmethyl)-4-methyl-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

HRID 2169554ノート

反応式

HRID 2169554 の反応式
[Cl:1][C:2]1[N:11]=[C:10]([CH3:12])[C:9]2[NH:8][CH2:7][CH:6]3[CH2:13][O:14][CH2:15][CH2:16][N:5]3[C:4]=2[N:3]=1.[CH3:17][C:18]([CH3:21])([O-])[CH3:19].[Na+].BrCC1CC1>CS(C)=O>[Cl:1][C:2]1[N:11]=[C:10]([CH3:12])[C:9]2[N:8]([CH2:17][CH:18]3[CH2:21][CH2:19]3)[CH2:7][CH:6]3[CH2:13][O:14][CH2:15][CH2:16][N:5]3[C:4]=2[N:3]=1

参加物

5

反応物 3

HCID 81503BromomethylcyclopropaneHCID 23676156Sodium t-butoxideHCID 866701002-Chloro-4-methyl-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

生成物 1

HCID 866701022-Chloro-5-(cyclopropylmethyl)-4-methyl-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine収率 18.4%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a round-bottom flask was added 2-chloro-4-methyl-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x20, 248 mg, 1.030 mmol) in DMSO (4 mL). Sodium tert-butoxide (119 mg, 1.236 mmol) was added, followed by (bromomethyl)cyclopropane (0.105 mL, 1.082 mmol), and the reaction mixture was stirred overnight at room temperature. The mixture was subsequently filtered and the filtrate was purified by preparatory HPLC using a gradient of 25-50% CH3CN (with 0.035% TFA) in H2O (with 0.05% TFA). The fractions were collected and concentrated in vacuo to give the title compound as a brown solid (56 mg, 0.190 mmol, 18%). ESI-MS m/z [M+H]+ calc'd for C14H19ClN4O, 295.12; found 295.6.

後処理

  1. filtrationThe mixture was subsequently filtered
  2. customthe filtrate was purified by preparatory HPLC
  3. customThe fractions were collected
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-eb7885bd26d24383b9f7dbed7678c405
出典データセット
uspto-grants-2015_06
特許番号
US09045496B2

反応ノート

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