Sodium ethoxide → 7-[(E)-2-(2-Cyclopropylmethoxy-3-methoxyphenyl)-1-ethenyl]-6-(4-difluoro methoxyphenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 1642441Notes

Reaction equation

HRID 1642441 reaction equation
[F:1][CH:2]([F:21])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15](=[O:16])[N:14]3[CH:17]=[CH:18][S:19][C:13]3=[N:12][C:11]=2[CH3:20])=[CH:6][CH:5]=1.[CH:22]1([CH2:25][O:26][C:27]2[C:34]([O:35][CH3:36])=[CH:33][CH:32]=[CH:31][C:28]=2[CH:29]=O)[CH2:24][CH2:23]1.[O-]CC.[Na+]>>[CH:22]1([CH2:25][O:26][C:27]2[C:34]([O:35][CH3:36])=[CH:33][CH:32]=[CH:31][C:28]=2/[CH:29]=[CH:20]/[C:11]2[N:12]=[C:13]3[S:19][CH:18]=[CH:17][N:14]3[C:15](=[O:16])[C:10]=2[C:7]2[CH:8]=[CH:9][C:4]([O:3][CH:2]([F:1])[F:21])=[CH:5][CH:6]=2)[CH2:23][CH2:24]1

Participants

4

Reactant 3

HCID 2723922Sodium ethoxideHCID 435604072-(Cyclopropylmethoxy)-3-methoxybenzaldehydeHCID 66752947HCID 66752947, compound

Product 1

HCID 444674637-[(E)-2-(2-Cyclopropylmethoxy-3-methoxyphenyl)-1-ethenyl]-6-(4-difluoro methoxyphenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneYield 39.2%

Procedure

The title compound was synthesized by condensation of Intermediate 14 (250 mg, 0.811 mmol) with 2-cyclopropylmethoxy-3-methoxybenzaldehyde (234 mg, 1.136 mmol) in presence of sodium ethoxide (110 mg, 1.623 mmol) according to the procedure of Example 23 to give 158 mg of the desired product; 1H NMR (300 MHz, DMSO-d6) δ 0.26-0.28 (m, 2H), 0.49-0.51 (m, 2H), 1.02-1.04 (m, 1H), 3.69 (m, 2H), 3.77 (s, 3H), 6.93-7.08 (m, 4H), 7.27-7.57 (m, 6H), 7.99 (br s, 1H), 8.15 (d, J=16.2 Hz, 1H); ESI-MS (m/z) 497.28 (M+H)+.

Sources & evidence

ORD record
ord-382bbc699f574b22ad5e0da14f43350d
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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