4-Chlorothieno[2,3-d]pyrimidine → 1-(4-(2-(3-Phenoxy-5-(thieno[2,3-d]pyrimidin-4-ylthio)pyridin-2-ylamino)thiazol-4-yl)piperidin-yl)ethanone

HRID 1809573Notes

Reaction equation

HRID 1809573 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[C:11]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[N:21]=[C:22]([NH:25][C:26]3[N:31]=[CH:30][C:29]([S:32]CCC(OC)=O)=[CH:28][C:27]=3[O:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[S:23][CH:24]=2)[CH2:16][CH2:15]1)(=[O:13])[CH3:12].CC([O-])(C)C.[K+]>CS(C)=O>[O:39]([C:27]1[C:26]([NH:25][C:22]2[S:23][CH:24]=[C:20]([CH:17]3[CH2:16][CH2:15][N:14]([C:11](=[O:13])[CH3:12])[CH2:19][CH2:18]3)[N:21]=2)=[N:31][CH:30]=[C:29]([S:32][C:2]2[C:3]3[CH:10]=[CH:9][S:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:28]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

5

Reactant 3

HCID 7366184-Chlorothieno[2,3-d]pyrimidineHCID 23665647Potassium tert-butoxideHCID 86631532Methyl 3-(6-(4-(1-acetylpiperidin-4-yl)thiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)propanoate

Product 1

HCID 577427911-(4-(2-(3-Phenoxy-5-(thieno[2,3-d]pyrimidin-4-ylthio)pyridin-2-ylamino)thiazol-4-yl)piperidin-yl)ethanoneYield 46%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-chlorothieno[2,3-d]pyrimidine (0.050 g, 0.29 mmol) and methyl 3-(6-(4-(1-acetylpiperidin-4-yl)thiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)propanoate (Example 3, Step B, 0.15 g, 0.29 mmol) were dissolved in DMSO (3 mL). The solution was degassed for 15 minutes. KOtBu (0.098 g, 0.88 mmol) was added and the reaction stirred at ambient temperature for two hours. The solution was quenched with water, extracted with dichloromethane, dried, and concentrated. Flash chromatography of the crude material gave the title compound (0.075, 46%). 1H NMR (400 MHz, CDCl3) δ 1.60-1.72 (m, 2H), 2.08-2.15 (m, 2H), 2.11 (m, 3H), 2.65-2.75 (m, 1H), 2.82-2.93 (m, 1H), 3.15-3.24 (m, 1H), 3.91 (d, 1H), 4.72 (d, 1H), 6.49 (s, 1H), 7.15 (d, 2H), 7.19 (t, 1H), 7.27-7.29 (m, 1H), 7.36-7.42 (m, 3H), 7.53 (d, 1H), 8.27 (d, 1H), 8.68 (s, 1H), 8.81 (s, 1H),

Workup

  1. customThe solution was degassed for 15 minutes
  2. customThe solution was quenched with water
  3. extractionextracted with dichloromethane
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-541d60bd965c45ad831031fa914d1147
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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