Trimethylamine → HCID 54508818, compound

HRID 1603303Notes

Reaction equation

HRID 1603303 reaction equation
CN(C)C.[F:5][C:6]1[C:11]([F:12])=[C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:9]=[CH:8][C:7]=1[C:22]1[N:27]=[CH:26][C:25]([OH:28])=[CH:24][N:23]=1.[Cl:29][C@@H:30]([C@@H:34]([CH3:37])[CH2:35][CH3:36])[C:31](Cl)=[O:32]>ClCCl>[F:5][C:6]1[C:11]([F:12])=[C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:9]=[CH:8][C:7]=1[C:22]1[N:23]=[CH:24][C:25]([O:28][C:31](=[O:32])[C@@H:30]([Cl:29])[C@@H:34]([CH3:37])[CH2:35][CH3:36])=[CH:26][N:27]=1

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 13651108HCID 13651108, compoundHCID 218324672-(2',3'-Difluoro-4'-octyloxyphenyl)-5-hydroxypyrimidine

Product 1

HCID 54508818HCID 54508818, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

--Trimethylamine (234 mg, 2.31 mmol) was added to a solution of the difluorophenylhydroxy-pyrimidine 35 (740 mg, 2.31 mmol) and (2S, 3S)-2-chloro-3-methylpentanoyl chloride 36 (388 mg, 2.31 mmol) in dry dichloromethane (8 ml) with stirring under nitrogen at room temperature for 2 h. Dichloromethane was added and the mixture was washed with dilute hydrochloric acid (twice), saturated sodium bicarbonate solution and brine, dried and evaporated. The residue was purified by flash chromatography (10% ethyl acetate-light petroleum) to give the ester 37 (670 mg, 58%) (from MeOH), m.p 66.2° C., [α]D26 +1.5° (c 2.4 in CHCl3); νmax /cm-1 (KBr) 2920, 1765 (CO), 1615, 1510, 1470, 1420, 1300, 1230, 1120 and 1080; δ 0.89 (3H, t,J6.5, Me), 1.00 (3H, t,J6.5, CH3CH2CH(CH3), 1.15 (3H, d,J7, CH(CH3)), 1.25-1.55 (10H, m), 1.76 (2H, m, CH3CH2CH(CH3), 1.85 (2H, quint, OCH2CH2), 2.25 (1H, m, CHMe), 4.11 (2H, d, J6.5, OCH2), 4.44 (1H, d, J7, CHCl), 6.84 (1H, ddd, J8, 7 and 2, 5'-H), 7.85 (1H, ddd, J8, 7 and 2, 6'-H) and 8.71 (2H, s 4- and 6-H); m/z 470 (M+), 468 (M+), 358 (M+ -C8H16), 356 (M+ -C8H16), 336, 237 and 224.

Workup

  1. washthe mixture was washed with dilute hydrochloric acid (twice), saturated sodium bicarbonate solution and brine
  2. customdried
  3. customevaporated
  4. customThe residue was purified by flash chromatography (10% ethyl acetate-light petroleum)

Sources & evidence

ORD record
ord-04b60a6224794698b386b53e71b8ef4d
Source dataset
uspto-grants-1999_11
Patent number
US05986096

Reaction notes

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