1,4-Bis(dihydroquinidine)phthalazine → (R)-4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbut-3-yne-1,2-diol

HRID 1984116Notes

Reaction equation

HRID 1984116 reaction equation
[Cl:1][C:2]1[C:3]2[C:11]([C:12]#CC(C)=C)=[CH:10][N:9]([CH2:17][C:18]3[C:23]([CH3:24])=[C:22]([O:25][CH3:26])[C:21]([CH3:27])=[CH:20][N:19]=3)[C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1.CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:49]C)C=C4)N(CC2)C1.[CH3:86][C:87]([OH:90])([CH3:89])[CH3:88].O>>[NH2:8][C:6]1[N:7]=[C:2]([Cl:1])[C:3]2[C:11]([C:12]#[C:86][C@@:87]([CH3:89])([OH:90])[CH2:88][OH:49])=[CH:10][N:9]([CH2:17][C:18]3[C:23]([CH3:24])=[C:22]([O:25][CH3:26])[C:21]([CH3:27])=[CH:20][N:19]=3)[C:4]=2[N:5]=1

Participants

4

Reactant 3

HCID 112172021,4-Bis(dihydroquinidine)phthalazineHCID 577138164-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-5-(3-methylbut-3-en-1-ynyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amineHCID 714019492-Methylpropan-2-ol--water (1/1)

Product 1

HCID 57713869(R)-4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbut-3-yne-1,2-diol

Procedure

Treatment of 4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-5-(3-methylbut-3-en-1-ynyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine (see example 51) (357 mg) with AD-mix-β (Aldrich, 1.57 g) in t-BuOH:water 1:1: (10 mL) at rt for 18 h, followed by quench (NaHSO3, 1.2 g), work-up, and silica gel flash chromatography (1→10% MeOH inDCM) gave the title compound (61 mg) and recovered starting material (263 mg).

Workup

  1. customby quench (NaHSO3, 1.2 g)

Sources & evidence

ORD record
ord-37dea16f9f8c4c1ea15cf44305b0a9f3
Source dataset
uspto-grants-2009_06
Patent number
US07544672B2

Reaction notes

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