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

HRID 1485504Notes

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

Participants

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

washthe reaction mixture was washed with brine
dry with materialAfter drying with MgSO4
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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