4-Hydroxy-4-methylpent-2-ynoic acid → (S)-1-(3-(4-amino-5-((3,5-dimethoxyphenyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidin-1-yl)-4-hydroxy-4-methylpent-2-yn-1-one

HRID 516165Notes

Reaction equation

HRID 516165 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]#[C:12][C:13]2[C:21]3[C:20]([NH2:22])=[N:19][CH:18]=[N:17][C:16]=3[N:15]([C@H:23]3[CH2:27][CH2:26][NH:25][CH2:24]3)[CH:14]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[OH:28][C:29]([CH3:36])([CH3:35])[C:30]#[C:31][C:32](O)=[O:33]>>[NH2:22][C:20]1[C:21]2[C:13]([C:12]#[C:11][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=3)=[CH:14][N:15]([C@H:23]3[CH2:27][CH2:26][N:25]([C:32](=[O:33])[C:31]#[C:30][C:29]([OH:28])([CH3:36])[CH3:35])[CH2:24]3)[C:16]=2[N:17]=[CH:18][N:19]=1

Participants

3

Reactant 2

HCID 31641664-Hydroxy-4-methylpent-2-ynoic acidHCID 89870819(S)-5-((3,5-dimethoxyphenyl)ethynyl)-7-(pyrrolidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 89870955(S)-1-(3-(4-amino-5-((3,5-dimethoxyphenyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidin-1-yl)-4-hydroxy-4-methylpent-2-yn-1-one

Procedure

In accordance with Example 4 (Step 1), except that (S)-5-((3,5-dimethoxyphenyl)ethynyl)-7-(pyrrolidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (i.e., the intermediate obtained in Example 38 (Step 4)) and 4-hydroxy-4-methylpent-2-ynoic acid were used, the title compound was obtained as a colorless, amorphous substance. Table 1 shows the physical properties thereof.

Sources & evidence

ORD record
ord-01a70de6124d4f1d94c9f00939a0db3c
Source dataset
uspto-grants-2015_08
Patent number
US09108973B2

Reaction notes

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