Sodium borohydride → (S)-tert-butyl 2-((4-(4-(4-(5-(hydroxy(phenyl)methyl)pyrimidin-2-yl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate

HRID 522654Notes

Reaction equation

HRID 522654 reaction equation
[C:1]([C:9]1[CH:10]=[N:11][C:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[N:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]4[CH:29]=[N:30][N:31]([CH2:33][C@H:34]5[O:39][CH2:38][CH2:37][N:36]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:35]5)[CH:32]=4)[N:22]=3)[CH2:17][CH2:16]2)=[N:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C1COCC1.CO>[OH:8][CH:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:10]=[N:11][C:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[N:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]4[CH:29]=[N:30][N:31]([CH2:33][C@H:34]5[O:39][CH2:38][CH2:37][N:36]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:35]5)[CH:32]=4)[N:22]=3)[CH2:17][CH2:16]2)=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 118022966(S)-tert-butyl 2-((4-(4-(4-(5-benzoylpyrimidin-2-yl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate

Product 1

HCID 118023167(S)-tert-butyl 2-((4-(4-(4-(5-(hydroxy(phenyl)methyl)pyrimidin-2-yl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of (S)-tert-butyl 2-((4-(4-(4-(5-benzoylpyrimidin-2-yl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate (80 mg, 0.127 mmol) in THF/methanol was added sodium borohydride (20 mg, 0.51 mmol). The mixture was stirred at room temperature for 1 hour, and LCMS showed the reaction was completed. The solvents were removed to give (S)-tert-butyl 2-((4-(4-(4-(5-(hydroxy(phenyl)methyl)pyrimidin-2-yl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate (80 mg, crude) as a yellowish solid. (MS (ES+) C31H39N11O4 requires: 629, found: 630 [M+H]+.

Workup

  1. customThe solvents were removed

Sources & evidence

ORD record
ord-b27d867f8a9940d4a0e5497649d66370
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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