Triphenylphosphine → HCID 23297048, compound

HRID 1954508Notes

Reaction equation

HRID 1954508 reaction equation
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

Participants

7

Reactant 5

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

Product 1

HCID 23297048HCID 23297048, compoundYield 140.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(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.

Workup

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

Sources & evidence

ORD record
ord-70067792ec954eb283b38557edefbf2b
Source dataset
uspto-grants-2000_09
Patent number
US06121448

Reaction notes

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