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Ethyl Acetate → (S)-1-(4-(benzylamino)-7-ethynylthieno[3,2-d]pyrimidin-2-ylamino)propan-2-ol

HRID 1485504
Notes
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Reaction equation

HRID 1485504 reaction equation
[CH2:1]([NH:8][C:9]1[C:10]2[S:18][CH:17]=[C:16]([C:19]#[CH:20])[C:11]=2[N:12]=[C:13](Cl)[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:21][CH2:22][C@@H:23]([OH:25])[CH3:24].C(OCC)(=O)C>O1CCOCC1>[CH2:1]([NH:8][C:9]1[C:10]2[S:18][CH:17]=[C:16]([C:19]#[CH:20])[C:11]=2[N:12]=[C:13]([NH:21][CH2:22][C@@H:23]([OH:25])[CH3:24])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 7311736(S)-(+)-1-Aminopropan-2-olHCID 86675659N-benzyl-2-chloro-7-ethynylthieno[3,2-d]pyrimidin-4-amine

Product 1

HCID 53239538(S)-1-(4-(benzylamino)-7-ethynylthieno[3,2-d]pyrimidin-2-ylamino)propan-2-olYield 52.3%

Reagents, catalysts & solvents 1

HCID 312751,4-Dioxane
Solvent

Conditions

Temperature
120 °C

Procedure

N-Benzyl-2-chloro-7-ethynylthieno[3,2-d]pyrimidin-4-amine (30 mg, 0.096 mmol) was dissolved in anhydrous dioxane (0.5 mL) and (S)-1-aminopropan-2-ol (23 μL, 0.288 mmol) was added. The reaction mixture was stirred at 120° C. for 24 hours. After adding ethyl acetate (3 mL), the reaction mixture was washed with brine. After drying with MgSO4 and concentrating by filtration, purification by silica gel chromatography (ethyl acetate/hexane:1/3→1/1) yielded the target compound of Example 44 (17 mg, 50% yield).

Workup

  1. washthe reaction mixture was washed with brine
  2. dry with materialAfter drying with MgSO4
  3. concentrationconcentrating by filtration, purification by silica gel chromatography (ethyl acetate/hexane:1/3→1/1)

Sources & evidence

ORD record
ord-9d66a8002ac840b5a63067327f44a0ea
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09422307B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes