Sodium hydride → 7-{(E)-2-[2-(Cyclopropylmethoxy)-3-methoxyphenyl]vinyl}-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 1642371Notes

Reaction equation

HRID 1642371 reaction equation
[Cl-].[O:2]=[C:3]1[N:8]2[CH:9]=[CH:10][S:11][C:7]2=[N:6][C:5]([CH2:12][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:4]1.[H-].[Na+].[CH:34]1([CH2:37][O:38][C:39]2[C:46]([O:47][CH3:48])=[CH:45][CH:44]=[CH:43][C:40]=2[CH:41]=O)[CH2:36][CH2:35]1>CS(C)=O.C(OCC)(=O)C>[CH:34]1([CH2:37][O:38][C:39]2[C:46]([O:47][CH3:48])=[CH:45][CH:44]=[CH:43][C:40]=2/[CH:41]=[CH:12]/[C:5]2[N:6]=[C:7]3[S:11][CH:10]=[CH:9][N:8]3[C:3](=[O:2])[CH:4]=2)[CH2:35][CH2:36]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 20260428((5-Oxo-5H-thiazolo[3,2-a]pyrimidin-7-yl)methyl)triphenylphosphoniumchlorideHCID 435604072-(Cyclopropylmethoxy)-3-methoxybenzaldehyde

Product 1

HCID 667534457-{(E)-2-[2-(Cyclopropylmethoxy)-3-methoxyphenyl]vinyl}-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of Step 2 intermediate (13.0 g, 28.08) was added NaH (1.2 g, 30.88) in dry DMSO (75 ml) and stirred for 0.5 h. A solution of 2-(cyclopropylmethoxy)-3-methoxybenzaldehyde (6.3 g, 30.88 mmol) in DMSO was added dropwise to this solution at room temperature and stirred for 2 h. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous Na2SO4 to yield a crude solid which was purified by column chromatography using 10% ethyl acetate in DCM to afford 7.5 g of the desired compound as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 0.30-0.33 (m, 2H), 0.52-057 (m, 2H), 1.10-1.20 (br m, 1H), 3.72-3.90 (m, 5H), 6.29 (s, 1H), 7.00-7.11 (m, 3H), 7.34 (d, J=6.3 Hz, 1H), 7.44-7.50 (m, 1H), 7.90-8.00 (m, 1H), 8.14 (d, J=6.2 Hz, 1H); ESI-MS (m/z) 355.17 (M+H)+

Workup

  1. stirringstirred for 2 h
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customto yield a crude solid which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-88ffd5f6ac0a49a6a016c2876730c42e
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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