Acetaldehyde → 1-(2-Chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)ethanol

HRID 2098768Notes

Reaction equation

HRID 2098768 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[CH:10]=[CH:9][S:8][C:6]=2[N:7]=1.[CH:17](=[O:19])[CH3:18]>>[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[CH:10]=[C:9]([CH:17]([OH:19])[CH3:18])[S:8][C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 177AcetaldehydeHCID 130381892-Chloro-4-(morpholin-4-yl)thieno(2,3-d)pyrimidine

Product 1

HCID 866184211-(2-Chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)ethanol

Procedure

2-chloro-4-morpholinothieno[2,3-d]pyrimidine (300 mg) was reacted with acetaldehyde via General Procedure D to give 1-(2-chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)ethanol. This crude intermediate was reacted with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)1H-indazole 7 via General Procedure A to yield 100.2 mg of 308 following reverse phase HPLC purification. MS (Q1) 382.1 (M)+

Sources & evidence

ORD record
ord-a0990d8fef3e4ed5ae5d0d98485b6121
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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