(2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methanol → (2-(5-fluoro-1H-indol-4-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methanol

HRID 1043569Notes

Reaction equation

HRID 1043569 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[N:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][C:6]=2[N:7]=1.[Si]([N:27]1[C:35]2[C:30](=[C:31](B3OC(C)(C)C(C)(C)O3)[C:32]([F:36])=[CH:33][CH:34]=2)[CH:29]=[CH:28]1)(C(C)(C)C)(C)C>>[F:36][C:32]1[C:31]([C:2]2[N:3]=[C:4]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:5]3[N:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][C:6]=3[N:7]=2)=[C:30]2[C:35](=[CH:34][CH:33]=1)[NH:27][CH:28]=[CH:29]2

Participants

3

Reactant 2

HCID 53488008(2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methanolHCID 575067251-(tert-Butyldimethylsilyl)-5-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Product 1

HCID 53378054(2-(5-fluoro-1H-indol-4-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methanol

Procedure

(2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methanol 6 (0.1 g) was reacted with 1-(tert-butyldimethylsilyl)-5-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole via General Procedure A to produce 73.4 mg of 108 following reverse phase HPLC purification. MS (Q1) 380.1 (M)+

Workup

  1. customto produce
  2. custom73.4 mg of 108 following reverse phase HPLC purification

Sources & evidence

ORD record
ord-9c15e37b3b9c4ad6b656dea5b64969b3
Source dataset
uspto-grants-2013_10
Patent number
US08563540B2

Reaction notes

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