1-Chloro-2-iodoethane → 5-(2-Ethylbenzoimidazol-1-yl)-2-iodo-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine

HRID 1922765

반응식

HRID 1922765 반응식
[CH2:1]([C:3]1[N:7]([C:8]2[N:9]=[C:10]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[C:11]3[N:16]=[CH:15][S:14][C:12]=3[N:13]=2)[C:6]2[CH:23]=[CH:24][CH:25]=[CH:26][C:5]=2[N:4]=1)[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.ClCC[I:40]>C1COCC1>[CH2:1]([C:3]1[N:7]([C:8]2[N:9]=[C:10]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[C:11]3[N:16]=[C:15]([I:40])[S:14][C:12]=3[N:13]=2)[C:6]2[CH:23]=[CH:24][CH:25]=[CH:26][C:5]=2[N:4]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 1364381-Chloro-2-iodoethaneHCID 2733832Lithium HexamethyldisilazideHCID 596056325-(2-Ethylbenzoimidazol-1-yl)-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine

생성물 1

HCID 596061865-(2-Ethylbenzoimidazol-1-yl)-2-iodo-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-5 °C

실험 절차

A solution of 5 -(2-ethylbenzoimidazol-1-yl)-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine (1.92 g, 5.23 mmol) in THF (60 mL) was cooled to −40° C. before the drop wise addition of LiHMDS (6.3 mL, 6.28 mmol, 1 M solution in THF). The resulting mixture was warmed to −5° C. over 30 min then mixture was cooled back to −30° C. before the addition of a solution of 1-chloro-2-iodoethane (2.0 g, 10.47 mmol) in THF (6 mL) The resulting mixture was allowed to warm to 0° C. then quenched with NH4Cl and extracted with EtOAc. The combined organics were washed with brine then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, EtOAc:DCM, 50-80%) followed by recrystallisation from iPrOAc affording the title compound as a yellow solid (1.58 g, 62%)._LCMS (method A): RT 3.50 min [M+H]+ 493.0

후처리

  1. temperatureto warm to 0° C.
  2. customthen quenched with NH4Cl
  3. extractionextracted with EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialthen dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si—PCC, EtOAc:DCM, 50-80%)
  8. customfollowed by recrystallisation from iPrOAc affording the title compound as a yellow solid (1.58 g, 62%)
  9. customRT 3.50 min [M+H]+ 493.0

출처 및 근거

ORD 기록
ord-2995dab65c564bfe9440a6e3e763c92e
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173650B2

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