Sodium borohydride → 6-~{tert}-Butyl-8-Fluoranyl-2-[3-(Hydroxymethyl)-4-[1-Methyl-6-Oxidanylidene-5-(Pyrimidin-4-Ylamino)pyridin-3-Yl]pyridin-2-Yl]phthalazin-1-One

HRID 407644Notes

Reaction equation

HRID 407644 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[N:24]=[CH:23][CH:22]=[C:21]([C:25]3[CH:30]=[C:29]([NH:31][C:32]4[CH:37]=[CH:36][N:35]=[CH:34][N:33]=4)[C:28](=[O:38])[N:27]([CH3:39])[CH:26]=3)[C:18]=1[CH:19]=[O:20])[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[C:18]([CH2:19][OH:20])=[C:21]([C:25]3[CH:30]=[C:29]([NH:31][C:32]4[CH:37]=[CH:36][N:35]=[CH:34][N:33]=4)[C:28](=[O:38])[N:27]([CH3:39])[CH:26]=3)[CH:22]=[CH:23][N:24]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866839322-(6-tert-Butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-(1-methyl-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridin-3-yl)nicotinaldehyde

Product 1

HCID 866839336-~{tert}-Butyl-8-Fluoranyl-2-[3-(Hydroxymethyl)-4-[1-Methyl-6-Oxidanylidene-5-(Pyrimidin-4-Ylamino)pyridin-3-Yl]pyridin-2-Yl]phthalazin-1-OneYield 77.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 113c (80 mg, 0.14 mmol), NaBH4 (27 mg, 0.70 mmol), and methanol (10 mL) was stirred at room temperature for 0.5 h. The mixture was quenched with water (2 mL) and concentrated under reduced pressure. The residue was purified with reverse-phase prep-HPLC to afford 113 (57 mg, 71%). MS-ESI: [M+H]+ 528.3. 1H NMR (500 MHz, DMSO-d6) δ 9.26 (s, 1H), 8.76 (d, J=2.5 Hz, 1H), 8.67 (s, 1H), 8.59 (d, J=5.0 Hz, 1H), 8.54 (d, J=2.5 Hz, 1H), 8.31 (d, J=6.0 Hz, 1H), 7.90 (d, J=1.5 Hz, 1H), 7.79-7.76 (m, 1H), 7.69 (d, J=2.0 Hz 1H), 7.54 (d, J=5.0, Hz 1H), 7.34-7.32 (m, 1H), 4.94 (t, J=5.0 Hz, 1H), 4.42-4.40 (m, 2H), 3.62 (s, 3H), 1.39 (s, 9H).

Workup

  1. customThe mixture was quenched with water (2 mL)
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified with reverse-phase prep-HPLC

Sources & evidence

ORD record
ord-5a25a8dab3414e68a4bbcbc078c84b64
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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