Triphenylphosphine → 2-Fluorooctyloxypyrimidine

HRID 1954508노트

반응식

HRID 1954508 반응식
CCOC(/N=N/C(OCC)=O)=O.[F:13][C@H:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][OH:16].O[C:24]1[N:29]=[CH:28][CH:27]=[CH:26][N:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC1C(F)=C(CCCCC)C=CC=1C1N=CC(OC[C@H](F)CCCCCC)=CN=1>C1COCC1>[F:13][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][O:16][C:24]1[N:29]=[CH:28][CH:27]=[CH:26][N:25]=1

참가 물질

7

반응물 5

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10855629(R)-(+)-2-fluorooctanolHCID 10993240HCID 10993240, 화합물HCID 178517760HCID 178517760, 화합물

생성물 1

HCID 232970482-Fluorooctyloxypyrimidine수율 140.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(R)-(31)-2-[2',3'-difluoro-4'-(trans-4"-pentylcyclohexylethyl)phenyl]-5-(2-fluorooctyloxy)pyrimidine 49.-Quantities: DEAD (448 mg, 2.58 mmol) in THF (3 ml), (R)-(+)-2-fluorooctanol (379 mg, 2.58 mmol), hydroxypyrimidine 48 (1.0 g, 2.58 mmol), triphenylphosphine (676 mg, 2.58 mmol). The experimental procedure was as described for compound 34. The crude product was purified by flash chromatography (5 to 7% ethyl acetate-light petroleum) to give the 2-fluorooctyloxypyrimidine 49 (820 mg, 61%) (from EtOH), transitions/° C. K 102.2 N* 128.3 I; [α]D26 -2.4° (c 2.0 in CHCl3); νmax /cm-1 (KBr) 2920, 2845, 1540, 1460, 1435s, 1285 1080, and 900; δ 0.80-1.03 (10 H, m), 1.06-1.45 (16H, m), 1.55 (4H, m), 1.82 (6 H, m), 2.71 (2 H, t J 8, ArCH2), 4.22 (2 H, dd, 3JHF 22 and J 4, OCH2), 4.86 (1 H, d of sext, 2JHF 48 and J 4, CHF), 7.01 (1 H, ddd, J 7.5, 7 and 1.5, 5'-H), 7.67 (1 H, ddd, J 7.5, 7 and 1.5, 5'-H), and 8.53 (2 H, s, 4- and 6-H); m/z 518 (M+), 489, 475, 461, 447, 365 and 353.

후처리

  1. customThe crude product was purified by flash chromatography (5 to 7% ethyl acetate-light petroleum)

출처 및 근거

ORD 기록
ord-70067792ec954eb283b38557edefbf2b
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06121448

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