Triphenylphosphine → 4-chloro-5-iodo-7-(1,4-dioxaspiro[4.5]decan-8-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 51566

반응식

HRID 51566 반응식
[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[O:12]1[C:16]2([CH2:21][CH2:20][CH:19](O)[CH2:18][CH2:17]2)[O:15][CH2:14][CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([CH:19]3[CH2:20][CH2:21][C:16]4([O:15][CH2:14][CH2:13][O:12]4)[CH2:17][CH2:18]3)[C:4]=2[N:5]=[CH:6][N:7]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5673521,4-Dioxaspiro(4.5)decan-8-olHCID 5462977Diethyl azodicarboxylateHCID 148092816-Chloro-7-iodo-7-deazapurine

생성물 1

HCID 227363864-chloro-5-iodo-7-(1,4-dioxaspiro[4.5]decan-8-yl)-7H-pyrrolo[2,3-d]pyrimidine수율 200.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (25.0 g, 0.09 mol), 1,4-dioxaspiro[4.5]decan-8-ol (35.8 g, 0.0267 mol) and triphenylphosphine (46.7 g, 0.178 mol) in THF (1.2 L) was added diethylazodicarboxylate (30.9 g, 0.178 mol) under nitrogen. The solution was stirred for 20 hr and the majority of solvent was then evaporated (250 mL remaining). EtOAc (450 mL) was then added and the resulting solid was filtered, washed with EtOAc (2×50 mL) and dried in vacuo to give 4-chloro-7-(1,4-dioxaspiro[4.5]dec-8-yl)-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (22.5 g, 60%) as a cream solid. 1H NMR (d6 DMSO, 400 MHz) 8.64(1H, s), 8.10(1H, s), 4.74(1H, m), 3.90(4H, m), 2.12(2H, m), 1.91(2H, m), 1,71-1.83(4H, m). Rf in 1:4 EtOAc:heptane=0.12.

후처리

  1. customthe majority of solvent was then evaporated (250 mL remaining)
  2. additionEtOAc (450 mL) was then added
  3. filtrationthe resulting solid was filtered
  4. washwashed with EtOAc (2×50 mL)
  5. customdried in vacuo

출처 및 근거

ORD 기록
ord-6a48710ce2474d33b87145bd56d37bbd
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713474B2

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