Ammonia → (S)-2-(1-((5-((5-Fluoro-2-hydroxyphenyl)thio)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052765Notes

Reaction equation

HRID 1052765 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:46]C)=[C:6]([S:8][C:9]2[C:17]3[C:16]([NH:18][C@H:19]([C:21]4[N:26]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[C:25](=[O:33])[C:24]5=[C:34]([CH3:37])[CH:35]=[CH:36][N:23]5[N:22]=4)[CH3:20])=[N:15][CH:14]=[N:13][C:12]=3[N:11](COCC[Si](C)(C)C)[CH:10]=2)[CH:7]=1.B(Br)(Br)Br.N>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:46])=[C:6]([S:8][C:9]2[C:17]3[C:16]([NH:18][C@H:19]([C:21]4[N:26]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[C:25](=[O:33])[C:24]5=[C:34]([CH3:37])[CH:35]=[CH:36][N:23]5[N:22]=4)[CH3:20])=[N:15][CH:14]=[N:13][C:12]=3[NH:11][CH:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 131736192(S)-2-(1-((5-((5-Fluoro-2-methoxyphenyl)thio)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 90102065(S)-2-(1-((5-((5-Fluoro-2-hydroxyphenyl)thio)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 69.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-(1-((5-((5-Fluoro-2-methoxyphenyl)thio)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (63 mg, 0.09 mmol) was treated with boron tribromide (1M in dichloromethane, 938 μl, 0.94 mmol) in dichloromethane (1.30 ml) and then with a solution of ammonia (7N in methanol, 1.30 ml, 9.10 mmol) according to the method described in Example 41. The residue was purified using SP1® Purification System (0% to 10% dichloromethane-2-propanol) to obtain 33 mg (64% yield) of the title compound.

Workup

  1. customThe residue was purified
  2. customSP1® Purification System (0% to 10% dichloromethane-2-propanol)

Sources & evidence

ORD record
ord-fb00184b30554910b7f808e2e4b13373
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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