(5-Phenyl-4-[(pyridin-2-ylmethyl)amino]thieno[2,3-d]pyrimidin-2-yl}acetic acid ethyl ester → 2-{5-Phenyl-4-[(pyridin-2-ylmethyl)amino]thieno[2,3-d]pyrimidin-2-yl}ethanol

HRID 910193Notes

Reaction equation

HRID 910193 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[N:7]=[C:8]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:9]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][S:12][C:10]=2[N:11]=1)C.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[C:15]1([C:14]2[C:9]3[C:8]([NH:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)=[N:7][C:6]([CH2:5][CH2:4][OH:3])=[N:11][C:10]=3[S:12][CH:13]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 11711155(5-Phenyl-4-[(pyridin-2-ylmethyl)amino]thieno[2,3-d]pyrimidin-2-yl}acetic acid ethyl esterHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 114398702-{5-Phenyl-4-[(pyridin-2-ylmethyl)amino]thieno[2,3-d]pyrimidin-2-yl}ethanolYield 55.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of {5-phenyl-4-[(pyridin-2-ylmethyl)amino]thieno[2,3-d]pyrimidin-2-yl}acetic acid ethyl ester (0.10 g, 0.248 mmol) in anhydrous tetrahydrofuran (1 ml) was cooled in an ice-bath and treated, under a nitrogen atmosphere, with diisobutylaluminium hydride (1M solution in hexane, 1.04 ml, 1.04 mmol) over about 15 minutes. The reaction mixture was allowed to warm up and left to stir at ambient temperature for 3 hours. The resultant mixture was then cooled in an ice-bath and quenched by the slow addition of methanol (0.5 ml) followed by water (1 ml). The mixture was then diluted with 2M sodium hydroxide solution (10 ml) and extracted with ethyl acetate (3×20 ml). The combined organic extracts were dried (MgSO4) and the solvent removed in vacuo to give the crude product. Purification by flash chromatography (silica) eluting with ethyl acetate and 40°-60° petroleum ether (4:1) gave 2-{5-phenyl-4-[(pyridin-2-ylmethyl)amino]thieno[2,3-d]pyrimidin-2-yl}ethanol as an off-white solid (0.05 g), m.p. 90°-92° C.

Workup

  1. temperatureto warm up
  2. waitleft
  3. customquenched by the slow addition of methanol (0.5 ml)
  4. additionThe mixture was then diluted with 2M sodium hydroxide solution (10 ml)
  5. extractionextracted with ethyl acetate (3×20 ml)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. customthe solvent removed in vacuo
  8. customto give the crude product
  9. customPurification by flash chromatography (silica)
  10. washeluting with ethyl acetate and 40°-60° petroleum ether (4:1)

Sources & evidence

ORD record
ord-f6323d70e88048e1836a14d713055cd3
Source dataset
uspto-grants-2011_09
Patent number
US08022076B2

Reaction notes

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