3-Hydroxypyridine → HCID 71667762, compound

HRID 1056851Notes

Reaction equation

HRID 1056851 reaction equation
[CH:1]1([N:4]([CH3:20])[C:5]2[C:6]3[C:15]4[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=4[S:13][C:7]=3[N:8]=[C:9]([CH2:11][OH:12])[N:10]=2)[CH2:3][CH2:2]1.O[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH:1]1([N:4]([CH3:20])[C:5]2[C:6]3[C:15]4[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=4[S:13][C:7]=3[N:8]=[C:9]([CH2:11][O:12][C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[N:10]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 79713-HydroxypyridineHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 71667761[4-(Cyclopropyl-methyl-amino)-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-2-yl]-methanol

Product 1

HCID 71667762HCID 71667762, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of [4-(cyclopropyl-methyl-amino)-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-2-yl]-methanol (0.25 g, 0.00086 mol), 3-hydroxypyridine (0.090 g, 0.00095 mol) & triphenylphosphine (0.24 g, 0.00095 mol) in THF (20 ml) was added DIAD (0.19 g, 0.00095 mol) in THF (5 ml), and the mixture was stirred at room temperature for 12 h. The reaction mixture was concentrated and the resulting crude material was purified by preparative HPLC to give cyclopropyl-methyl-[2-(pyridine-3-yloxymethyl)-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-yl]-amine (35 mg, 11%) as a brown residue. 1H NMR (400 MHz, CDCl3): δ 0.35-0.42 (m, 2H), 0.62-0.68 (m, 2H), 1.72-1.78 (m, 2H), 1.88-1.97 (m, 2H), 2.80-2.90 (m, 5H), 3.00 (s, 3H), 5.24 (s, 2H), 7.16 (dd, 1H), 7.30 (dd, 1H), 8.17 (dd, 1H), 8.42 (d, 1H); LC-MS: [M+H]=367.3 m/z.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-8dee65db858444c7a55fd4383e3cfc18
Source dataset
uspto-grants-2016_07
Patent number
US09399647B2

Reaction notes

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