Sodium hydride → N-(cyclopropylmethyl)-6-(3-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine

HRID 1049913Notes

Reaction equation

HRID 1049913 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH2:18])[C:16]=3[N:17]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH:22]1[CH2:25][CH2:24][CH2:23]1>>[CH:22]1([NH:18][C:15]2[C:16]3[N:17]=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=4)[CH:9]=[CH:10][C:11]=3[N:12]=[CH:13][N:14]=2)[CH2:25][CH2:24][CH2:23]1.[CH:25]1([CH2:22][NH:18][C:15]2[C:16]3[N:17]=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=4)[CH:9]=[CH:10][C:11]=3[N:12]=[CH:13][N:14]=2)[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 78110BromocyclobutaneHCID 867039146-(3-Fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine

Product 2

HCID 72703722N-(cyclopropylmethyl)-6-(3-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amineHCID 86703916N-cyclobutyl-6-(3-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine

Procedure

Following the same reaction and purification procedure, the amine 1 (100 mg, 0.42 mmol) was treated with sodium hydride 60% dispersion in mineral oil (25 mg, 0.62 mmol) and bromocyclobutane (56 mg, 0.42 mmol) to provide N-cyclobutyl-6-(3-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine 27 and N-(cyclopropylmethyl)-6-(3-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine 28. LC/MS (ESI+): m/z 295 (M+H). 1H NMR (400 MHz, DMSO) δ 8.80 (t, J=6.1 Hz, 1H), 8.48 (d, J=7.2 Hz, 2H), 8.39 (d, J=10.9 Hz, 1H), 8.22 (d, J=7.9 Hz, 1H), 8.15 (d, J=8.8 Hz, 1H), 7.60 (dd, J=14.3, 7.9 Hz, 1H), 7.34 (td, J=8.5, 2.4 Hz, 1H), 3.50 (t, J=6.5 Hz, 2H), 1.27 (dd, J=13.4, 6.1 Hz, 1H), 0.52-0.42 (m, 2H), 0.42-0.31 (m, 2H).

Workup

  1. customthe same reaction and purification procedure

Sources & evidence

ORD record
ord-5767d9bcbe7d47579476ad773e917ac5
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

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