N-Iodosuccinimide → 7-iodo-2,4-bis-benzyloxy-5H-pyrrolo[3,2-d]pyrimidine

HRID 57785ノート

反応式

HRID 57785 の反応式
[CH2:1]([O:8][C:9]1[N:10]=[C:11]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:12]2[NH:17][CH:16]=[CH:15][C:13]=2[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)N([I:33])C(=O)C1>C(Cl)Cl>[I:33][C:15]1[C:13]2[N:14]=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[N:10]=[C:11]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:12]=2[NH:17][CH:16]=1

参加物

4

反応物 2

HCID 120273N-IodosuccinimideHCID 109255905H-Pyrrolo3,2-dpyrimidine, 2,4-bis(phenylmethoxy)-

生成物 1

HCID 718123077-iodo-2,4-bis-benzyloxy-5H-pyrrolo[3,2-d]pyrimidine収率 90.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 2,4-bis-O-benzyl-5H-pyrrolo[3,2-d]pyrimidine 15 (1.43 g, 4.3 mmol) in anhydrous CH2Cl2 (15 mL) under N2, NIS (1.069 g, 4.7 mmol) was added at which point the reaction mixture turned from pink to orange. The mixture was stirred overnight until the TLC indicated the absence of starting material. The reaction mixture was washed with aqueous Na2S2O3 (15 mL) followed by brine (15 mL). The organic layer was dried over MgSO4, loaded onto silica and purified using column chromatography eluting with 4:1 then 1:1 hexanes/EtOAc to obtain compound 16 as a pale-yellow solid (1.77 g, 3.88 mmol, 90%). Rf 0.4 in 1:3 hexanes/EtOAc. Mp 157.8-158.4° C. 1H NMR (400 MHz, CDCl3): δ 5.53 (s, 4H), 7.32-7.41 (m, 9H), 7.55-7.57 (m, 2H), 8.71 (br s, 1H, NH). 13C NMR: 57.3, 68.7, 69.3, 111.9, 127.9, 128.3, 128.6, 128.66, 128.7, 128.9, 132.4, 135.8, 137.2, 152.0, 156.9, 160.1. FAB-MS m/z for C20H16IN3O2 calculated [M+H]+ 458.0360. found 458.0357.

後処理

  1. washThe reaction mixture was washed with aqueous Na2S2O3 (15 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. custompurified
  4. washeluting with 4:1

出典と根拠

ORDレコード
ord-26985f8cc72d4e9cbc8579654c24fc41
出典データセット
uspto-grants-2016_09
特許番号
US09434742B1

反応ノート

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