Cesium fluoride → {(3R)-4-[4-(2-aminopyrimidin-5-yl)-7-(3,3-difluorocyclobutyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-2-yl]morpholin-3-yl}methanol

HRID 1775474Notes

Reaction equation

HRID 1775474 reaction equation
[F:1][C:2]1([F:25])[CH2:5][CH:4]([N:6]2[C:10]3[N:11]=[C:12](S(C)=O)[N:13]=[C:14]([C:15]4[CH:16]=[N:17][C:18]([NH2:21])=[N:19][CH:20]=4)[C:9]=3[CH2:8][CH2:7]2)[CH2:3]1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][C@H:27]1[CH2:32][OH:33].[F-].[Cs+]>C(#N)C>[NH2:21][C:18]1[N:17]=[CH:16][C:15]([C:14]2[C:9]3[CH2:8][CH2:7][N:6]([CH:4]4[CH2:5][C:2]([F:25])([F:1])[CH2:3]4)[C:10]=3[N:11]=[C:12]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][C@H:27]3[CH2:32][OH:33])[N:13]=2)=[CH:20][N:19]=1

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 1514269(R)-3-HydroxymethylmorpholineHCID 1184363685-[7-(3,3-difluorocyclobutyl)-2-(methylsulfinyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]pyrimidin-2-amine

Product 1

HCID 118436675{(3R)-4-[4-(2-aminopyrimidin-5-yl)-7-(3,3-difluorocyclobutyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-2-yl]morpholin-3-yl}methanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-[7-(3,3-difluorocyclobutyl)-2-(methylsulfinyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]pyrimidin-2-amine (35 mg, 0.096 mmol) in acetonitrile (0.3 mL) was added (3R)-morpholin-3-ylmethanol (68 mg, 0.576 mmol) and CsF (56 mg, 0.288 mmol), and the reaction mixture was sealed and heated at 120° C. for 96 h.

Workup

  1. customthe reaction mixture was sealed

Sources & evidence

ORD record
ord-98abb41f6b15459195f192cf1c4c685a
Source dataset
uspto-grants-2016_02
Patent number
US09260439B2

Reaction notes

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