3-Pyridinemethanamine → 2-Chloro-5-fluoro-N-(3-pyridinylmethyl)-4-pyrimidinamine

HRID 1932098Notes

Reaction equation

HRID 1932098 reaction equation
C1COC2C=CC(NC3C(F)=CN=C(NC4C=CC=C(O)C=4)N=3)=CC=2O1.[N:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][NH2:34])[CH:28]=1.[Cl:35][C:36]1[N:41]=[C:40](Cl)[C:39]([F:43])=[CH:38][N:37]=1>>[Cl:35][C:36]1[N:41]=[C:40]([NH:34][CH2:33][C:29]2[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=2)[C:39]([F:43])=[CH:38][N:37]=1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 22060334N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-primidinediamine

Product 1

HCID 220609912-Chloro-5-fluoro-N-(3-pyridinylmethyl)-4-pyrimidinamine

Procedure

In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 3-pyridylmethylamine (162 mg, 1.5 mmol) and 2,4-dichloro-5-fluoropyrimidine (50 mg, 0.3 mmol) were reacted to give 2-chloro-5-fluoro-N4-(3-pyridylmethyl)-4-pyrimidineamine. Then 2-chloro-5-fluoro-N4-(3-pyridylmethyl)-4-pyrimidineamine and 3-aminophenol (200 mg, 1.83 mmol) reacted to give 5-fluoro-N2-(3-hydroxyphenyl)-N4-(3-pyridylmethyl)-2,4-pyrimidinediamine (40 mg, 43%). 1H NMR (CD3OD): δ 4.71 (s, 2H), 6.38 (ddd, J=0.9, 2.4 and 8.1 Hz, 1H), 6.88 (ddd, J=0.9, 2.1 and 8.1 Hz, 1H), 7.00 (t, J=8.1 Hz, 1H), 7.14 (t, J=2.4 Hz, 1H), 7.37 (dd, J=4.8 and 7.8 Hz, 1H), 7.73 (d, J=3.6 Hz, 1H), 7.87 (dt, J=2.1 and 7.5 Hz, 1H), 8.39 (dd, J=1.2 and 7.8 Hz, 1H), 8.57 (d, J=2.1 Hz, 1H); 19F NMR (282 MHz, CD3OD): δ −170.99; LCMS: ret. time: 8.82 min.; purity: 92.90%; MS (m/e): 312.05 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-b2b8787d7411416e92e88ea2bc4b5fce
Source dataset
uspto-grants-2012_05
Patent number
US08188276B2

Reaction notes

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