Sodium Hydroxide → HCID 9809899, compound

HRID 411289Notes

Reaction equation

HRID 411289 reaction equation
[CH2:1]([N:13]([C:15]([CH2:17][N:18]1[CH:23]=[C:22]([CH2:24][C:25]2[CH:26]=[N:27][C:28](=[O:37])[N:29]([CH2:31][C:32]([O:34]CC)=[O:33])[CH:30]=2)[C:21](=[O:38])[N:20]=[C:19]1[S:39][CH2:40][C:41]1[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=1)=[O:16])[CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[OH-].[Na+]>O1CCOCC1.O>[CH2:1]([N:13]([C:15]([CH2:17][N:18]1[CH:23]=[C:22]([CH2:24][C:25]2[CH:26]=[N:27][C:28](=[O:37])[N:29]([CH2:31][C:32]([OH:34])=[O:33])[CH:30]=2)[C:21](=[O:38])[N:20]=[C:19]1[S:39][CH2:40][C:41]1[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=1)=[O:16])[CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 9896094HCID 9896094, compound

Product 1

HCID 9809899HCID 9809899, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a stirring solution of 1-(N-(1-dodecyl)-N-methylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(1-ethoxycarbonylmethyl-2-oxopyrimid-5-ylmethyl)pyrimidin-4-one in 1,4-dioxan (8 ml) was added 0.5M sodium hydroxide (1.56 ml). After 1 h, water (3 ml) was added. After a further hour, the mixture was diluted with water, extracted with ethyl acetate and acidified to pH 3 with aq. sodium bisulphate. The solid which precipitated was filtered, washed with water and ether, heated briefly with acetone and filtered again to give the product as a white solid, yield 0.28 g. 1H-NMR (d6-DMSO) δ0.85 (3H, t), 1.22 (18H, m), 1.35-1.61 (2H, m,), 2.78, 2.95 (3H, 2xs), 3.20-3.35 (2H, m), 3.58 (2H, s), 4.40 (2H, s), 4.55 (2H, s), 4.83 (2H, m), 7.10 (2H, m), 7.44 (2H, m), 7.54 and 7.57 (1H, 2xs), 8.03 (1H, m), 8.54 (1H, m) 13.10 (1H, br. s); MS (APCI+) found (M+1)=642, C33H44FN5O5S requires 641.

Workup

  1. waitAfter a further hour
  2. extractionextracted with ethyl acetate
  3. customThe solid which precipitated
  4. filtrationwas filtered
  5. washwashed with water and ether
  6. temperatureheated briefly with acetone
  7. filtrationfiltered again

Sources & evidence

ORD record
ord-500d92576f144b09aaf9814914bf06f9
Source dataset
uspto-grants-2003_05
Patent number
US06559155B1

Reaction notes

Loading…