Methyl iodide → HCID 58109228, compound

HRID 2046007Notes

Reaction equation

HRID 2046007 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([CH2:30][CH2:31][CH2:32][OH:33])[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][N:26]=[C:25]([OH:29])[N:24]=4)=[CH:19][CH:18]=3)[CH3:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:34]C([Si](Cl)(C)C)(C)C.[H-].[Na+].CI.[N+](CC)(CC)(CC)CC.[F-]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@:8]2([CH2:30][CH2:31][CH2:32][OH:33])[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][N:26]([CH3:34])[C:25](=[O:29])[N:24]=4)=[CH:19][CH:18]=3)[CH3:16])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 69582Ethanaminium, N,N,N-triethyl-, fluoride (1:1)HCID 178461657HCID 178461657, compound

Product 1

HCID 58109228HCID 58109228, compound

Procedure

The title compound was prepared from (R)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-3-((S)-1-(4-(2-hydroxypyrimidin-4-yl)phenyl)ethyl)-1,3-oxazinan-2-one by treatment with (i) TBSCl, (ii) NaH, MeI and (iii) Et4NF. LC-MS Method 2 tR=1.079 min, m/z=466.2; 1H NMR (CD3OD) 1.20 (m, 3H), 1.49 (d, 3H), 1.78-1.91 (m, 2H), 2.08 (s, 1H), 2.14 (m, 1H), 2.28 (m, 1H), 2.39 (m, 1H), 3.07 (m, 1H), 3.36 (m, 3H), 3.50 (s, 3H), 4.50 (s, 2H), 5.49 (m, 1H), 6.90 (d, 1H), 6.95-7.08 (m, 4H), 7.21 (m, 2H), 7.80 (d, 2H), 8.06 (d, 1H).

Sources & evidence

ORD record
ord-093ed36df59a4b26b822873eec036149
Source dataset
uspto-grants-2013_11
Patent number
US08592410B2

Reaction notes

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